# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_8.7%P_0.5GPa
_database_code_depnum_ccdc_archive 'CCDC 1491722'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_8.7%P_0.5GPa        
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.325 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_8.7%P_0.5GPa        
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#==================================================================== 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   31.07(4)
_cell_length_b                   10.5077(13)
_cell_length_c                   8.5590(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2794(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    1269
_cell_measurement_theta_min      6.66
_cell_measurement_theta_max      23.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.11732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).

ABSORB-GUI - analytical corrections for the diamond-anvil cell 
[Angel R.J. & Gonzalez-Platas J. (2013). J. Appl. Cryst. 
46, 252-254].
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            11138
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_av_R_equivalents  0.2076
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.688
_diffrn_reflns_theta_max         24.464
_diffrn_reflns_theta_full        24.464
_diffrn_measured_fraction_theta_max 0.325
_diffrn_measured_fraction_theta_full 0.325
_diffrn_reflns_Laue_measured_fraction_max 0.325
_diffrn_reflns_Laue_measured_fraction_full 0.325
_diffrn_reflns_point_group_measured_fraction_max 0.325
_diffrn_reflns_point_group_measured_fraction_full 0.325
_reflns_number_total             751
_reflns_number_gt                375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1952P)²+2.3663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         751
_refine_ls_number_parameters     89
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2111
_refine_ls_R_factor_gt           0.1183
_refine_ls_wR_factor_ref         0.3792
_refine_ls_wR_factor_gt          0.3153
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.4575(5) 0.7560(6) 0.0020(7) 0.084(11) Uani 1 1 d D . . . .
C2M C 0.4167(5) 0.6254(8) 0.1873(11) 0.072(3) Uiso 1 1 d D . . . .
H2M H 0.4125 0.6778 0.2808 0.086 Uiso 1 1 calc R U . A 1
C6M C 0.3778(9) 0.6299(11) 0.0982(12) 0.088(4) Uiso 1 1 d . . . . .
H6M1 H 0.3790 0.5662 0.0162 0.105 Uiso 1 1 calc R U . . .
H6M2 H 0.3752 0.7127 0.0491 0.105 Uiso 1 1 calc R U . . .
C7M C 0.3397(4) 0.6064(7) 0.1972(9) 0.084(3) Uiso 1 1 d G . . . .
C8M C 0.3194(5) 0.4866(6) 0.1942(9) 0.095(4) Uiso 1 1 d G . . . .
H8M H 0.3307 0.4220 0.1276 0.115 Uiso 1 1 d G U . . .
C9M C 0.2838(5) 0.4591(7) 0.2845(11) 0.120(5) Uiso 1 1 d G . . . .
H9M H 0.2712 0.3764 0.2808 0.144 Uiso 1 1 d G U . . .
C10M C 0.2665(5) 0.5532(9) 0.3808(10) 0.143(6) Uiso 1 1 d G . . . .
H10M H 0.2419 0.5348 0.4427 0.172 Uiso 1 1 d G U . . .
C11M C 0.2854(5) 0.6762(7) 0.3871(9) 0.110(5) Uiso 1 1 d G . . . .
H11M H 0.2735 0.7408 0.4520 0.132 Uiso 1 1 d G U . . .
C12M C 0.3222(5) 0.7009(5) 0.2956(10) 0.098(4) Uiso 1 1 d G . . . .
H12M H 0.3354 0.7828 0.3004 0.118 Uiso 1 1 d G U . . .
C1M C 0.4565(6) 0.6756(9) 0.1019(11) 0.061(2) Uiso 0.912(9) 1 d D U P B 1
C3M C 0.4333(6) 0.4929(8) 0.2413(12) 0.061(2) Uiso 0.912(9) 1 d D U P B 1
H3M1 H 0.4194 0.4684 0.3382 0.074 Uiso 0.912(9) 1 calc R U P B 1
H3M2 H 0.4268 0.4291 0.1628 0.074 Uiso 0.912(9) 1 calc R U P B 1
C4M C 0.4824(6) 0.5030(9) 0.2654(11) 0.061(2) Uiso 0.912(9) 1 d D U P B 1
H4M1 H 0.4892 0.5176 0.3745 0.074 Uiso 0.912(9) 1 calc R U P B 1
H4M2 H 0.4967 0.4260 0.2308 0.074 Uiso 0.912(9) 1 calc R U P B 1
C5M C 0.4953(6) 0.6138(8) 0.1678(10) 0.061(2) Uiso 0.912(9) 1 d D U P B 1
C13M C 0.5350(6) 0.6588(9) 0.1324(11) 0.062(3) Uiso 0.912(9) 1 d D U P B 1
H13M H 0.5351 0.7211 0.0552 0.075 Uiso 0.912(9) 1 calc R U P B 1
C14M C 0.5771(5) 0.6283(7) 0.1916(9) 0.059(3) Uiso 0.912(9) 1 d DG U P B 1
C15M C 0.5849(5) 0.5360(7) 0.3099(8) 0.075(4) Uiso 0.912(9) 1 d DG U P B 1
H15M H 0.5614 0.4896 0.3527 0.091 Uiso 0.912(9) 1 d G U P B 1
C16M C 0.6272(6) 0.5121(6) 0.3647(8) 0.082(4) Uiso 0.912(9) 1 d G U P B 1
H16M H 0.6322 0.4497 0.4434 0.098 Uiso 0.912(9) 1 d G U P B 1
C17M C 0.6618(5) 0.5808(8) 0.3024(10) 0.088(4) Uiso 0.912(9) 1 d G U P B 1
H17M H 0.6902 0.5662 0.3403 0.105 Uiso 0.912(9) 1 d G U P B 1
C18M C 0.6545(5) 0.6707(7) 0.1845(10) 0.086(4) Uiso 0.912(9) 1 d G U P B 1
H18M H 0.6779 0.7172 0.1421 0.103 Uiso 0.912(9) 1 d G U P B 1
C19M C 0.6127(5) 0.6924(6) 0.1289(8) 0.072(4) Uiso 0.912(9) 1 d DG U P B 1
H19M H 0.6083 0.7519 0.0467 0.086 Uiso 0.912(9) 1 d G U P B 1
C1D C 0.4546(12) 0.660(3) 0.087(6) 0.058(9) Uiso 0.088(9) 1 d D U P B 2
C3D C 0.4335(12) 0.523(5) 0.296(5) 0.058(9) Uiso 0.088(9) 1 d D U P B 2
H3D1 H 0.4216 0.4406 0.2679 0.070 Uiso 0.088(9) 1 calc R U P B 2
H3D2 H 0.4261 0.5417 0.4031 0.070 Uiso 0.088(9) 1 calc R U P B 2
C4D C 0.4823(11) 0.524(6) 0.273(3) 0.058(9) Uiso 0.088(9) 1 d D U P B 2
H4D1 H 0.4948 0.4423 0.3022 0.070 Uiso 0.088(9) 1 calc R U P B 2
H4D2 H 0.4957 0.5904 0.3347 0.070 Uiso 0.088(9) 1 calc R U P B 2
C5D C 0.4870(7) 0.549(2) 0.098(2) 0.058(9) Uiso 0.088(9) 1 d D U P B 2
C13D C 0.5286(7) 0.566(3) 0.008(4) 0.075(18) Uiso 0.088(9) 1 d D U P B 2
H13D H 0.5257 0.6434 -0.0542 0.090 Uiso 0.088(9) 1 calc R U P B 2
C14D C 0.5702(12) 0.576(5) 0.096(6) 0.047(16) Uiso 0.088(9) 1 d DG U P B 2
C15D C 0.5807(19) 0.510(6) 0.236(7) 0.09(2) Uiso 0.088(9) 1 d DG U P B 2
H15D H 0.5612 0.4483 0.2769 0.113 Uiso 0.088(9) 1 d G U P B 2
C16D C 0.620(2) 0.536(8) 0.315(8) 0.068(11) Uiso 0.088(9) 1 d G U P B 2
H16D H 0.6265 0.4905 0.4086 0.082 Uiso 0.088(9) 1 d G U P B 2
C17D C 0.6484(19) 0.627(8) 0.256(9) 0.076(11) Uiso 0.088(9) 1 d G U P B 2
H17D H 0.6744 0.6457 0.3101 0.092 Uiso 0.088(9) 1 d G U P B 2
C18D C 0.6386(16) 0.691(7) 0.117(9) 0.09(2) Uiso 0.088(9) 1 d G U P B 2
H18D H 0.6580 0.7533 0.0771 0.103 Uiso 0.088(9) 1 d G U P B 2
C19D C 0.6003(14) 0.664(6) 0.038(7) 0.083(19) Uiso 0.088(9) 1 d DG U P B 2
H19D H 0.5945 0.7067 -0.0575 0.100 Uiso 0.088(9) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1M 1.203(9) . ?
O1M C1D 1.245(15) . ?
C2M C6M 1.43(3) . ?
C2M C1D 1.503(10) . ?
C2M C3D 1.515(10) . ?
C2M C1M 1.530(15) . ?
C2M C3M 1.555(12) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.48(3) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.4072 . ?
C7M C12M 1.4110 . ?
C8M C9M 1.3805 . ?
C8M H8M 0.9527 . ?
C9M C10M 1.3949 . ?
C9M H9M 0.9546 . ?
C10M C11M 1.4205 . ?
C10M H10M 0.9512 . ?
C11M C12M 1.4097 . ?
C11M H11M 0.9526 . ?
C12M H12M 0.9539 . ?
C1M C5M 1.480(15) . ?
C3M C4M 1.543(18) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.488(12) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.357(15) . ?
C13M C14M 1.437(14) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.4018 . ?
C14M C15M 1.4231 . ?
C15M C16M 1.4186 . ?
C15M H15M 0.9498 . ?
C16M C17M 1.3990 . ?
C16M H16M 0.9528 . ?
C17M C18M 1.4008 . ?
C17M H17M 0.9532 . ?
C18M C19M 1.4014 . ?
C18M H18M 0.9481 . ?
C19M H19M 0.9522 . ?
C1D C5D 1.545(16) . ?
C3D C4D 1.526(11) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.536(18) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.512(17) . ?
C5D C13D 1.583(14) 5_665 ?
C13D C14D 1.500(17) . ?
C13D C5D 1.583(14) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.4083 . ?
C14D C15D 1.4194 . ?
C15D C16D 1.4166 . ?
C15D H15D 0.9541 . ?
C16D C17D 1.4053 . ?
C16D H16D 0.9504 . ?
C17D C18D 1.3974 . ?
C17D H17D 0.9517 . ?
C18D C19D 1.3992 . ?
C18D H18D 0.9524 . ?
C19D H19D 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6M C2M C1D 110(2) . . ?
C6M C2M C3D 130(2) . . ?
C1D C2M C3D 104.6(8) . . ?
C6M C2M C1M 114.7(10) . . ?
C6M C2M C3M 117.9(11) . . ?
C1M C2M C3M 100.5(10) . . ?
C6M C2M H2M 107.7 . . ?
C1M C2M H2M 107.7 . . ?
C3M C2M H2M 107.7 . . ?
C2M C6M C7M 111.5(8) . . ?
C2M C6M H6M1 109.3 . . ?
C7M C6M H6M1 109.3 . . ?
C2M C6M H6M2 109.3 . . ?
C7M C6M H6M2 109.3 . . ?
H6M1 C6M H6M2 108.0 . . ?
C8M C7M C12M 117.9 . . ?
C8M C7M C6M 119.8(7) . . ?
C12M C7M C6M 122.2(7) . . ?
C9M C8M C7M 122.4 . . ?
C9M C8M H8M 118.7 . . ?
C7M C8M H8M 118.9 . . ?
C8M C9M C10M 119.4 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.4 . . ?
C9M C10M C11M 120.5 . . ?
C9M C10M H10M 119.7 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.5 . . ?
C10M C11M H11M 120.7 . . ?
C11M C12M C7M 120.9 . . ?
C11M C12M H12M 119.4 . . ?
C7M C12M H12M 119.7 . . ?
O1M C1M C5M 123.9(13) . . ?
O1M C1M C2M 127.1(13) . . ?
C5M C1M C2M 109.0(8) . . ?
C4M C3M C2M 107.8(10) . . ?
C4M C3M H3M1 110.1 . . ?
C2M C3M H3M1 110.1 . . ?
C4M C3M H3M2 110.1 . . ?
C2M C3M H3M2 110.1 . . ?
H3M1 C3M H3M2 108.5 . . ?
C5M C4M C3M 104.2(10) . . ?
C5M C4M H4M1 110.9 . . ?
C3M C4M H4M1 110.9 . . ?
C5M C4M H4M2 110.9 . . ?
C3M C4M H4M2 110.9 . . ?
H4M1 C4M H4M2 108.9 . . ?
C13M C5M C1M 120.2(9) . . ?
C13M C5M C4M 130.0(12) . . ?
C1M C5M C4M 109.7(11) . . ?
C5M C13M C14M 132.1(9) . . ?
C5M C13M H13M 113.9 . . ?
C14M C13M H13M 113.9 . . ?
C19M C14M C15M 117.7 . . ?
C19M C14M C13M 118.4(7) . . ?
C15M C14M C13M 123.9(7) . . ?
C16M C15M C14M 121.0 . . ?
C16M C15M H15M 119.5 . . ?
C14M C15M H15M 119.5 . . ?
C17M C16M C15M 119.6 . . ?
C17M C16M H16M 120.1 . . ?
C15M C16M H16M 120.3 . . ?
C16M C17M C18M 119.9 . . ?
C16M C17M H17M 119.9 . . ?
C18M C17M H17M 120.2 . . ?
C17M C18M C19M 120.3 . . ?
C17M C18M H18M 119.9 . . ?
C19M C18M H18M 119.8 . . ?
C18M C19M C14M 121.6 . . ?
C18M C19M H19M 119.4 . . ?
C14M C19M H19M 119.0 . . ?
O1M C1D C2M 125.9(16) . . ?
O1M C1D C5D 126.8(15) . . ?
C2M C1D C5D 107.1(9) . . ?
C2M C3D C4D 105.3(9) . . ?
C2M C3D H3D1 110.7 . . ?
C4D C3D H3D1 110.7 . . ?
C2M C3D H3D2 110.7 . . ?
C4D C3D H3D2 110.7 . . ?
H3D1 C3D H3D2 108.8 . . ?
C3D C4D C5D 102.6(11) . . ?
C3D C4D H4D1 111.2 . . ?
C5D C4D H4D1 111.2 . . ?
C3D C4D H4D2 111.2 . . ?
C5D C4D H4D2 111.2 . . ?
H4D1 C4D H4D2 109.2 . . ?
C13D C5D C4D 127(2) . . ?
C13D C5D C1D 116(2) . . ?
C4D C5D C1D 97.3(14) . . ?
C13D C5D C13D 93.6(14) . 5_665 ?
C4D C5D C13D 114(2) . 5_665 ?
C1D C5D C13D 110(2) . 5_665 ?
C14D C13D C5D 119(3) . . ?
C14D C13D C5D 127(3) . 5_665 ?
C5D C13D C5D 86.4(14) . 5_665 ?
C14D C13D H13D 107.1 . . ?
C5D C13D H13D 107.1 . . ?
C5D C13D H13D 107.1 5_665 . ?
C19D C14D C15D 117.9 . . ?
C19D C14D C13D 116(2) . . ?
C15D C14D C13D 126(2) . . ?
C16D C15D C14D 120.5 . . ?
C16D C15D H15D 119.8 . . ?
C14D C15D H15D 119.7 . . ?
C17D C16D C15D 119.9 . . ?
C17D C16D H16D 120.3 . . ?
C15D C16D H16D 119.9 . . ?
C18D C17D C16D 120.0 . . ?
C18D C17D H17D 119.8 . . ?
C16D C17D H17D 120.2 . . ?
C17D C18D C19D 119.8 . . ?
C17D C18D H18D 120.1 . . ?
C19D C18D H18D 120.1 . . ?
C18D C19D C14D 121.8 . . ?
C18D C19D H19D 119.0 . . ?
C14D C19D H19D 119.2 . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_26.2%P_0.5GPa
_database_code_depnum_ccdc_archive 'CCDC 1491723'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_ATOM007_26.2%P_0.5GPa       
;
PROBLEM: atom_site_aniso_label is missing 
         Unique label identifying the atom site.

RESPONSE: The treatment of all atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
_vrf_PLAT029_26.2%P_0.5GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.297 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_26.2%P_0.5GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         20 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   31.16(6)
_cell_length_b                   10.4812(19)
_cell_length_c                   8.5557(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2794(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    886
_cell_measurement_theta_min      6.67
_cell_measurement_theta_max      23.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.58732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).

ABSORB-GUI - analytical corrections for the diamond-anvil cell 
[Angel R.J. & Gonzalez-Platas J. (2013). J. Appl. Cryst. 
46, 252-254].
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            9980
_diffrn_reflns_av_unetI/netI     0.1217
_diffrn_reflns_av_R_equivalents  0.2225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.692
_diffrn_reflns_theta_max         24.482
_diffrn_reflns_theta_full        24.482
_diffrn_measured_fraction_theta_max 0.297
_diffrn_measured_fraction_theta_full 0.297
_diffrn_reflns_Laue_measured_fraction_max 0.297
_diffrn_reflns_Laue_measured_fraction_full 0.297
_diffrn_reflns_point_group_measured_fraction_max 0.297
_diffrn_reflns_point_group_measured_fraction_full 0.297
_reflns_number_total             688
_reflns_number_gt                313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         688
_refine_ls_number_parameters     82
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2434
_refine_ls_R_factor_gt           0.1371
_refine_ls_wR_factor_ref         0.4245
_refine_ls_wR_factor_gt          0.3601
_refine_ls_goodness_of_fit_ref   1.316
_refine_ls_restrained_S_all      1.297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.4552(6) 0.7499(6) 0.0028(9) 0.094(3) Uiso 1 1 d D . . . .
C2M C 0.4155(6) 0.6223(9) 0.1922(13) 0.080(4) Uiso 1 1 d D . . . .
H2M H 0.4125 0.6731 0.2877 0.096 Uiso 1 1 calc R U . A 1
C6M C 0.3752(10) 0.6288(11) 0.1090(12) 0.089(4) Uiso 1 1 d . . . . .
H6M1 H 0.3721 0.7130 0.0634 0.107 Uiso 1 1 calc R U . . .
H6M2 H 0.3755 0.5671 0.0246 0.107 Uiso 1 1 calc R U . . .
C7M C 0.3397(5) 0.6039(8) 0.2083(9) 0.087(4) Uiso 1 1 d G . . . .
C8M C 0.3199(6) 0.4835(7) 0.2059(10) 0.107(4) Uiso 1 1 d G . . . .
H8M H 0.3312 0.4192 0.1390 0.128 Uiso 1 1 d G U . . .
C9M C 0.2845(6) 0.4549(8) 0.2971(11) 0.139(6) Uiso 1 1 d G . . . .
H9M H 0.2722 0.3717 0.2939 0.166 Uiso 1 1 d G U . . .
C10M C 0.2671(5) 0.5484(11) 0.3939(9) 0.157(7) Uiso 1 1 d G . . . .
H10M H 0.2426 0.5292 0.4564 0.188 Uiso 1 1 d G U . . .
C11M C 0.2855(6) 0.6720(9) 0.3996(10) 0.122(5) Uiso 1 1 d G . . . .
H11M H 0.2735 0.7363 0.4649 0.146 Uiso 1 1 d G U . . .
C12M C 0.3221(6) 0.6979(6) 0.3072(11) 0.105(5) Uiso 1 1 d G . . . .
H12M H 0.3350 0.7802 0.3116 0.126 Uiso 1 1 d G U . . .
C1M C 0.4552(7) 0.6685(12) 0.1088(14) 0.063(3) Uiso 0.738(11) 1 d D U P B 1
C3M C 0.4316(8) 0.4896(11) 0.2404(18) 0.063(3) Uiso 0.738(11) 1 d D U P B 1
H3M1 H 0.4171 0.4611 0.3344 0.076 Uiso 0.738(11) 1 calc R U P B 1
H3M2 H 0.4262 0.4282 0.1578 0.076 Uiso 0.738(11) 1 calc R U P B 1
C4M C 0.4798(8) 0.5031(19) 0.2698(19) 0.063(3) Uiso 0.738(11) 1 d D U P B 1
H4M1 H 0.4854 0.5235 0.3785 0.076 Uiso 0.738(11) 1 calc R U P B 1
H4M2 H 0.4947 0.4246 0.2439 0.076 Uiso 0.738(11) 1 calc R U P B 1
C5M C 0.4942(7) 0.6081(12) 0.1672(14) 0.063(3) Uiso 0.738(11) 1 d D U P B 1
C13M C 0.5331(8) 0.6570(12) 0.1324(15) 0.063(3) Uiso 0.738(11) 1 d D U P B 1
H13M H 0.5322 0.7228 0.0596 0.076 Uiso 0.738(11) 1 calc R U P B 1
C14M C 0.5758(7) 0.6274(11) 0.1854(13) 0.062(5) Uiso 0.738(11) 1 d DG U P B 1
C15M C 0.5861(7) 0.5352(10) 0.3014(13) 0.076(5) Uiso 0.738(11) 1 d DG U P B 1
H15M H 0.5637 0.4867 0.3478 0.091 Uiso 0.738(11) 1 d G U P B 1
C16M C 0.6293(8) 0.5148(10) 0.3485(15) 0.090(5) Uiso 0.738(11) 1 d G U P B 1
H16M H 0.6359 0.4524 0.4256 0.108 Uiso 0.738(11) 1 d G U P B 1
C17M C 0.6623(7) 0.5867(13) 0.2808(18) 0.104(7) Uiso 0.738(11) 1 d G U P B 1
H17M H 0.6913 0.5744 0.3135 0.125 Uiso 0.738(11) 1 d G U P B 1
C18M C 0.6526(7) 0.6766(12) 0.1652(16) 0.101(7) Uiso 0.738(11) 1 d G U P B 1
H18M H 0.6749 0.7253 0.1191 0.121 Uiso 0.738(11) 1 d G U P B 1
C19M C 0.6099(8) 0.6949(10) 0.1172(13) 0.074(5) Uiso 0.738(11) 1 d DG U P B 1
H19M H 0.6038 0.7544 0.0363 0.089 Uiso 0.738(11) 1 d G U P B 1
C1D C 0.4504(9) 0.6493(19) 0.077(3) 0.055(6) Uiso 0.262(11) 1 d D U P B 2
C3D C 0.4287(12) 0.506(3) 0.280(4) 0.055(6) Uiso 0.262(11) 1 d D U P B 2
H3D1 H 0.4164 0.4297 0.2342 0.066 Uiso 0.262(11) 1 calc R U P B 2
H3D2 H 0.4198 0.5113 0.3889 0.066 Uiso 0.262(11) 1 calc R U P B 2
C4D C 0.4776(12) 0.505(5) 0.267(3) 0.055(6) Uiso 0.262(11) 1 d D U P B 2
H4D1 H 0.4895 0.4211 0.2880 0.066 Uiso 0.262(11) 1 calc R U P B 2
H4D2 H 0.4908 0.5671 0.3361 0.066 Uiso 0.262(11) 1 calc R U P B 2
C5D C 0.4824(7) 0.5424(17) 0.0950(19) 0.055(6) Uiso 0.262(11) 1 d D U P B 2
C13D C 0.5264(6) 0.5722(18) 0.022(3) 0.055(6) Uiso 0.262(11) 1 d D U P B 2
H13D H 0.5243 0.6527 -0.0361 0.066 Uiso 0.262(11) 1 calc R U P B 2
C14D C 0.5654(9) 0.577(3) 0.126(3) 0.081(12) Uiso 0.262(11) 1 d DG U P B 2
C15D C 0.5708(11) 0.488(3) 0.248(3) 0.076(9) Uiso 0.262(11) 1 d DG U P B 2
H15D H 0.5486 0.4271 0.2691 0.091 Uiso 0.262(11) 1 d G U P B 2
C16D C 0.6087(14) 0.487(3) 0.340(4) 0.096(9) Uiso 0.262(11) 1 d G U P B 2
H16D H 0.6120 0.4266 0.4217 0.116 Uiso 0.262(11) 1 d G U P B 2
C17D C 0.6413(12) 0.577(4) 0.310(5) 0.087(13) Uiso 0.262(11) 1 d G U P B 2
H17D H 0.6666 0.5780 0.3731 0.105 Uiso 0.262(11) 1 d G U P B 2
C18D C 0.6366(10) 0.664(3) 0.189(4) 0.073(13) Uiso 0.262(11) 1 d G U P B 2
H18D H 0.6586 0.7248 0.1681 0.087 Uiso 0.262(11) 1 d G U P B 2
C19D C 0.5994(10) 0.663(3) 0.096(3) 0.085(13) Uiso 0.262(11) 1 d DG U P B 2
H19D H 0.5969 0.7210 0.0120 0.102 Uiso 0.262(11) 1 d G U P B 2

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1D 1.242(15) . ?
O1M C1M 1.246(12) . ?
C2M C6M 1.45(3) . ?
C2M C1D 1.491(18) . ?
C2M C3D 1.492(18) . ?
C2M C1M 1.506(16) . ?
C2M C3M 1.535(15) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.42(3) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.4051 . ?
C7M C12M 1.4097 . ?
C8M C9M 1.3828 . ?
C8M H8M 0.9517 . ?
C9M C10M 1.3935 . ?
C9M H9M 0.9530 . ?
C10M C11M 1.4183 . ?
C10M H10M 0.9526 . ?
C11M C12M 1.4120 . ?
C11M H11M 0.9518 . ?
C12M H12M 0.9524 . ?
C1M C5M 1.459(16) . ?
C3M C4M 1.531(19) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.477(15) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.350(16) . ?
C13M C14M 1.439(16) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.4034 . ?
C14M C15M 1.4213 . ?
C15M C16M 1.4218 . ?
C15M H15M 0.9507 . ?
C16M C17M 1.4005 . ?
C16M H16M 0.9515 . ?
C17M C18M 1.3990 . ?
C17M H17M 0.9553 . ?
C18M C19M 1.4046 . ?
C18M H18M 0.9492 . ?
C19M H19M 0.9510 . ?
C1D C5D 1.509(17) . ?
C3D C4D 1.53(2) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.531(18) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.539(17) . ?
C5D C13D 1.586(13) 5_665 ?
C13D C14D 1.508(16) . ?
C13D C5D 1.586(13) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.4080 . ?
C14D C15D 1.4184 . ?
C15D C16D 1.4192 . ?
C15D H15D 0.9539 . ?
C16D C17D 1.4047 . ?
C16D H16D 0.9497 . ?
C17D C18D 1.3963 . ?
C17D H17D 0.9537 . ?
C18D C19D 1.4018 . ?
C18D H18D 0.9522 . ?
C19D H19D 0.9493 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6M C2M C1D 107.4(15) . . ?
C6M C2M C3D 121.8(19) . . ?
C1D C2M C3D 106.8(15) . . ?
C6M C2M C1M 117.7(11) . . ?
C6M C2M C3M 117.2(13) . . ?
C1M C2M C3M 98.7(12) . . ?
C6M C2M H2M 107.5 . . ?
C1M C2M H2M 107.5 . . ?
C3M C2M H2M 107.5 . . ?
C7M C6M C2M 112.0(9) . . ?
C7M C6M H6M1 109.2 . . ?
C2M C6M H6M1 109.2 . . ?
C7M C6M H6M2 109.2 . . ?
C2M C6M H6M2 109.2 . . ?
H6M1 C6M H6M2 107.9 . . ?
C8M C7M C12M 117.8 . . ?
C8M C7M C6M 119.9(8) . . ?
C12M C7M C6M 122.3(8) . . ?
C9M C8M C7M 122.4 . . ?
C9M C8M H8M 118.8 . . ?
C7M C8M H8M 118.8 . . ?
C8M C9M C10M 119.6 . . ?
C8M C9M H9M 120.2 . . ?
C10M C9M H9M 120.2 . . ?
C9M C10M C11M 120.3 . . ?
C9M C10M H10M 119.8 . . ?
C11M C10M H10M 119.9 . . ?
C12M C11M C10M 118.9 . . ?
C12M C11M H11M 120.6 . . ?
C10M C11M H11M 120.5 . . ?
C7M C12M C11M 121.0 . . ?
C7M C12M H12M 119.5 . . ?
C11M C12M H12M 119.5 . . ?
O1M C1M C5M 123.1(15) . . ?
O1M C1M C2M 124.4(15) . . ?
C5M C1M C2M 112.5(10) . . ?
C4M C3M C2M 106.2(13) . . ?
C4M C3M H3M1 110.5 . . ?
C2M C3M H3M1 110.5 . . ?
C4M C3M H3M2 110.5 . . ?
C2M C3M H3M2 110.5 . . ?
H3M1 C3M H3M2 108.7 . . ?
C5M C4M C3M 105.6(12) . . ?
C5M C4M H4M1 110.6 . . ?
C3M C4M H4M1 110.6 . . ?
C5M C4M H4M2 110.6 . . ?
C3M C4M H4M2 110.6 . . ?
H4M1 C4M H4M2 108.7 . . ?
C13M C5M C1M 120.6(11) . . ?
C13M C5M C4M 133.3(14) . . ?
C1M C5M C4M 105.9(13) . . ?
C5M C13M C14M 132.8(12) . . ?
C5M C13M H13M 113.6 . . ?
C14M C13M H13M 113.6 . . ?
C19M C14M C15M 117.5 . . ?
C19M C14M C13M 117.4(9) . . ?
C15M C14M C13M 125.1(9) . . ?
C14M C15M C16M 120.9 . . ?
C14M C15M H15M 119.3 . . ?
C16M C15M H15M 119.7 . . ?
C17M C16M C15M 119.8 . . ?
C17M C16M H16M 119.9 . . ?
C15M C16M H16M 120.3 . . ?
C18M C17M C16M 119.7 . . ?
C18M C17M H17M 120.2 . . ?
C16M C17M H17M 120.1 . . ?
C17M C18M C19M 120.3 . . ?
C17M C18M H18M 119.8 . . ?
C19M C18M H18M 120.0 . . ?
C14M C19M C18M 121.8 . . ?
C14M C19M H19M 118.9 . . ?
C18M C19M H19M 119.4 . . ?
O1M C1D C2M 126.0(15) . . ?
O1M C1D C5D 127.0(18) . . ?
C2M C1D C5D 106.0(11) . . ?
C2M C3D C4D 104.0(19) . . ?
C2M C3D H3D1 111.0 . . ?
C4D C3D H3D1 111.0 . . ?
C2M C3D H3D2 111.0 . . ?
C4D C3D H3D2 111.0 . . ?
H3D1 C3D H3D2 109.0 . . ?
C3D C4D C5D 99.6(18) . . ?
C3D C4D H4D1 111.8 . . ?
C5D C4D H4D1 111.8 . . ?
C3D C4D H4D2 111.8 . . ?
C5D C4D H4D2 111.8 . . ?
H4D1 C4D H4D2 109.6 . . ?
C1D C5D C4D 102.8(15) . . ?
C1D C5D C13D 113.4(16) . . ?
C4D C5D C13D 122.0(19) . . ?
C1D C5D C13D 112.6(18) . 5_665 ?
C4D C5D C13D 113(2) . 5_665 ?
C13D C5D C13D 92.9(13) . 5_665 ?
C14D C13D C5D 119.1(19) . . ?
C14D C13D C5D 122(2) . 5_665 ?
C5D C13D C5D 87.1(13) . 5_665 ?
C14D C13D H13D 108.8 . . ?
C5D C13D H13D 108.8 . . ?
C5D C13D H13D 108.8 5_665 . ?
C19D C14D C15D 117.7 . . ?
C19D C14D C13D 121.5(16) . . ?
C15D C14D C13D 120.6(16) . . ?
C14D C15D C16D 120.6 . . ?
C14D C15D H15D 119.5 . . ?
C16D C15D H15D 119.9 . . ?
C17D C16D C15D 120.0 . . ?
C17D C16D H16D 120.1 . . ?
C15D C16D H16D 119.9 . . ?
C18D C17D C16D 119.9 . . ?
C18D C17D H17D 119.9 . . ?
C16D C17D H17D 120.3 . . ?
C17D C18D C19D 119.9 . . ?
C17D C18D H18D 119.9 . . ?
C19D C18D H18D 120.2 . . ?
C18D C19D C14D 121.9 . . ?
C18D C19D H19D 119.1 . . ?
C14D C19D H19D 119.0 . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_35.4%P_0.5GPa
_database_code_depnum_ccdc_archive 'CCDC 1491724'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_35.4%P_0.5GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.322 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_35.4%P_0.5GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   31.05(5)
_cell_length_b                   10.4910(16)
_cell_length_c                   8.5775(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2794(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    1036
_cell_measurement_theta_min      6.67
_cell_measurement_theta_max      23.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.60619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).

ABSORB-GUI - analytical corrections for the diamond-anvil cell 
[Angel R.J. & Gonzalez-Platas J. (2013). J. Appl. Cryst. 
46, 252-254].
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            11162
_diffrn_reflns_av_unetI/netI     0.1241
_diffrn_reflns_av_R_equivalents  0.2347
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.685
_diffrn_reflns_theta_max         24.426
_diffrn_reflns_theta_full        24.426
_diffrn_measured_fraction_theta_max 0.322
_diffrn_measured_fraction_theta_full 0.322
_diffrn_reflns_Laue_measured_fraction_max 0.322
_diffrn_reflns_Laue_measured_fraction_full 0.322
_diffrn_reflns_point_group_measured_fraction_max 0.322
_diffrn_reflns_point_group_measured_fraction_full 0.322
_reflns_number_total             740
_reflns_number_gt                353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         740
_refine_ls_number_parameters     87
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2364
_refine_ls_R_factor_gt           0.1329
_refine_ls_wR_factor_ref         0.4351
_refine_ls_wR_factor_gt          0.3763
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_restrained_S_all      1.337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.4541(6) 0.7467(6) 0.0037(8) 0.122(15) Uani 1 1 d D . . . .
C2M C 0.4149(6) 0.6224(8) 0.1944(13) 0.088(4) Uiso 1 1 d D . . . .
H2M H 0.4127 0.6744 0.2890 0.105 Uiso 1 1 calc R U . A 1
C6M C 0.3722(10) 0.6265(11) 0.1161(12) 0.091(4) Uiso 1 1 d . . . . .
H6M1 H 0.3682 0.7102 0.0705 0.109 Uiso 1 1 calc R U . . .
H6M2 H 0.3721 0.5648 0.0319 0.109 Uiso 1 1 calc R U . . .
C7M C 0.3382(5) 0.6012(9) 0.2140(10) 0.107(5) Uiso 1 1 d G . . . .
C8M C 0.3184(5) 0.4808(7) 0.2120(9) 0.121(5) Uiso 1 1 d G . . . .
H8M H 0.3297 0.4164 0.1453 0.145 Uiso 1 1 d G U . . .
C9M C 0.2830(6) 0.4526(7) 0.3033(12) 0.135(5) Uiso 1 1 d G . . . .
H9M H 0.2707 0.3694 0.3003 0.162 Uiso 1 1 d G U . . .
C10M C 0.2656(5) 0.5464(11) 0.3997(10) 0.173(7) Uiso 1 1 d G . . . .
H10M H 0.2412 0.5273 0.4623 0.208 Uiso 1 1 d G U . . .
C11M C 0.2841(6) 0.6699(8) 0.4050(10) 0.141(6) Uiso 1 1 d G . . . .
H11M H 0.2721 0.7344 0.4701 0.169 Uiso 1 1 d G U . . .
C12M C 0.3206(6) 0.6955(6) 0.3125(12) 0.122(5) Uiso 1 1 d G . . . .
H12M H 0.3336 0.7777 0.3166 0.146 Uiso 1 1 d G U . . .
C1M C 0.4538(7) 0.6685(14) 0.1057(17) 0.074(3) Uiso 0.646(12) 1 d D U P B 1
C3M C 0.4309(9) 0.4866(12) 0.2455(19) 0.074(3) Uiso 0.646(12) 1 d D U P B 1
H3M1 H 0.4161 0.4583 0.3389 0.089 Uiso 0.646(12) 1 calc R U P B 1
H3M2 H 0.4263 0.4246 0.1632 0.089 Uiso 0.646(12) 1 calc R U P B 1
C4M C 0.4794(9) 0.506(2) 0.277(2) 0.074(3) Uiso 0.646(12) 1 d D U P B 1
H4M1 H 0.4842 0.5330 0.3838 0.089 Uiso 0.646(12) 1 calc R U P B 1
H4M2 H 0.4953 0.4282 0.2581 0.089 Uiso 0.646(12) 1 calc R U P B 1
C5M C 0.4931(7) 0.6073(13) 0.1668(16) 0.074(3) Uiso 0.646(12) 1 d D U P B 1
C13M C 0.5314(8) 0.6580(13) 0.1271(17) 0.074(3) Uiso 0.646(12) 1 d D U P B 1
H13M H 0.5299 0.7247 0.0558 0.089 Uiso 0.646(12) 1 calc R U P B 1
C14M C 0.5743(7) 0.6260(13) 0.1769(14) 0.068(5) Uiso 0.646(12) 1 d DG U P B 1
C15M C 0.5862(8) 0.5355(11) 0.2928(14) 0.098(7) Uiso 0.646(12) 1 d DG U P B 1
H15M H 0.5646 0.4852 0.3413 0.118 Uiso 0.646(12) 1 d G U P B 1
C16M C 0.6298(8) 0.5193(12) 0.3368(16) 0.083(5) Uiso 0.646(12) 1 d G U P B 1
H16M H 0.6375 0.4580 0.4140 0.100 Uiso 0.646(12) 1 d G U P B 1
C17M C 0.6617(7) 0.5937(15) 0.266(2) 0.121(8) Uiso 0.646(12) 1 d G U P B 1
H17M H 0.6910 0.5843 0.2966 0.145 Uiso 0.646(12) 1 d G U P B 1
C18M C 0.6503(8) 0.6819(14) 0.1504(18) 0.097(6) Uiso 0.646(12) 1 d G U P B 1
H18M H 0.6719 0.7324 0.1022 0.116 Uiso 0.646(12) 1 d G U P B 1
C19M C 0.6072(8) 0.6960(11) 0.1055(13) 0.076(6) Uiso 0.646(12) 1 d DG U P B 1
H19M H 0.6001 0.7545 0.0246 0.091 Uiso 0.646(12) 1 d G U P B 1
C1D C 0.4499(8) 0.6484(17) 0.079(2) 0.061(5) Uiso 0.354(12) 1 d D U P B 2
C3D C 0.4277(10) 0.5092(19) 0.291(2) 0.061(5) Uiso 0.354(12) 1 d D U P B 2
H3D1 H 0.4128 0.4331 0.2562 0.073 Uiso 0.354(12) 1 calc R U P B 2
H3D2 H 0.4213 0.5234 0.4001 0.073 Uiso 0.354(12) 1 calc R U P B 2
C4D C 0.4763(10) 0.497(3) 0.265(3) 0.061(5) Uiso 0.354(12) 1 d D U P B 2
H4D1 H 0.4923 0.5511 0.3356 0.073 Uiso 0.354(12) 1 calc R U P B 2
H4D2 H 0.4858 0.4091 0.2785 0.073 Uiso 0.354(12) 1 calc R U P B 2
C5D C 0.4816(6) 0.5399(15) 0.0956(16) 0.061(5) Uiso 0.354(12) 1 d D U P B 2
C13D C 0.5259(6) 0.5722(15) 0.026(2) 0.061(5) Uiso 0.354(12) 1 d D U P B 2
H13D H 0.5232 0.6531 -0.0301 0.073 Uiso 0.354(12) 1 calc R U P B 2
C14D C 0.5668(7) 0.577(2) 0.118(2) 0.070(9) Uiso 0.354(12) 1 d DG U P B 2
C15D C 0.5731(8) 0.4862(19) 0.239(2) 0.075(9) Uiso 0.354(12) 1 d DG U P B 2
H15D H 0.5512 0.4248 0.2603 0.090 Uiso 0.354(12) 1 d G U P B 2
C16D C 0.6115(10) 0.486(2) 0.328(3) 0.093(8) Uiso 0.354(12) 1 d G U P B 2
H16D H 0.6154 0.4245 0.4085 0.112 Uiso 0.354(12) 1 d G U P B 2
C17D C 0.6436(9) 0.577(3) 0.298(4) 0.108(11) Uiso 0.354(12) 1 d G U P B 2
H17D H 0.6692 0.5781 0.3587 0.130 Uiso 0.354(12) 1 d G U P B 2
C18D C 0.6379(8) 0.665(2) 0.178(3) 0.081(8) Uiso 0.354(12) 1 d G U P B 2
H18D H 0.6597 0.7269 0.1569 0.097 Uiso 0.354(12) 1 d G U P B 2
C19D C 0.6003(8) 0.664(2) 0.088(2) 0.089(11) Uiso 0.354(12) 1 d DG U P B 2
H19D H 0.5972 0.7230 0.0049 0.106 Uiso 0.354(12) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1M 1.199(12) . ?
O1M C1D 1.224(14) . ?
C2M C6M 1.49(3) . ?
C2M C1D 1.492(17) . ?
C2M C3D 1.501(17) . ?
C2M C1M 1.505(16) . ?
C2M C3M 1.571(15) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.37(3) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.4052 . ?
C7M C12M 1.4109 . ?
C8M C9M 1.3810 . ?
C8M H8M 0.9525 . ?
C9M C10M 1.3946 . ?
C9M H9M 0.9532 . ?
C10M C11M 1.4186 . ?
C10M H10M 0.9513 . ?
C11M C12M 1.4100 . ?
C11M H11M 0.9525 . ?
C12M H12M 0.9525 . ?
C1M C5M 1.477(16) . ?
C3M C4M 1.544(19) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.481(15) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.347(16) . ?
C13M C14M 1.437(16) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.4015 . ?
C14M C15M 1.4235 . ?
C15M C16M 1.4176 . ?
C15M H15M 0.9496 . ?
C16M C17M 1.3987 . ?
C16M H16M 0.9530 . ?
C17M C18M 1.4012 . ?
C17M H17M 0.9526 . ?
C18M C19M 1.4006 . ?
C18M H18M 0.9480 . ?
C19M H19M 0.9525 . ?
C1D C5D 1.513(17) . ?
C3D C4D 1.53(2) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.530(17) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.536(16) . ?
C5D C13D 1.591(13) 5_665 ?
C13D C14D 1.496(16) . ?
C13D C5D 1.591(13) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.4060 . ?
C14D C15D 1.4208 . ?
C15D C16D 1.4167 . ?
C15D H15D 0.9526 . ?
C16D C17D 1.4029 . ?
C16D H16D 0.9513 . ?
C17D C18D 1.3988 . ?
C17D H17D 0.9521 . ?
C18D C19D 1.3995 . ?
C18D H18D 0.9509 . ?
C19D H19D 0.9510 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6M C2M C1D 110.1(13) . . ?
C6M C2M C3D 120.5(15) . . ?
C1D C2M C3D 108.5(14) . . ?
C6M C2M C1M 118.5(11) . . ?
C6M C2M C3M 115.7(13) . . ?
C1M C2M C3M 100.3(12) . . ?
C6M C2M H2M 107.2 . . ?
C1M C2M H2M 107.2 . . ?
C3M C2M H2M 107.2 . . ?
C7M C6M C2M 113.8(9) . . ?
C7M C6M H6M1 108.8 . . ?
C2M C6M H6M1 108.8 . . ?
C7M C6M H6M2 108.8 . . ?
C2M C6M H6M2 108.8 . . ?
H6M1 C6M H6M2 107.7 . . ?
C6M C7M C8M 120.2(9) . . ?
C6M C7M C12M 121.9(9) . . ?
C8M C7M C12M 117.9 . . ?
C9M C8M C7M 122.3 . . ?
C9M C8M H8M 118.8 . . ?
C7M C8M H8M 118.9 . . ?
C8M C9M C10M 119.5 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.4 . . ?
C9M C10M C11M 120.4 . . ?
C9M C10M H10M 119.8 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.6 . . ?
C10M C11M H11M 120.6 . . ?
C11M C12M C7M 121.0 . . ?
C11M C12M H12M 119.4 . . ?
C7M C12M H12M 119.6 . . ?
O1M C1M C5M 123.3(16) . . ?
O1M C1M C2M 126.5(17) . . ?
C5M C1M C2M 110.1(11) . . ?
C4M C3M C2M 103.6(13) . . ?
C4M C3M H3M1 111.0 . . ?
C2M C3M H3M1 111.0 . . ?
C4M C3M H3M2 111.0 . . ?
C2M C3M H3M2 111.0 . . ?
H3M1 C3M H3M2 109.0 . . ?
C5M C4M C3M 105.4(13) . . ?
C5M C4M H4M1 110.7 . . ?
C3M C4M H4M1 110.7 . . ?
C5M C4M H4M2 110.7 . . ?
C3M C4M H4M2 110.7 . . ?
H4M1 C4M H4M2 108.8 . . ?
C13M C5M C1M 118.0(12) . . ?
C13M C5M C4M 134.2(15) . . ?
C1M C5M C4M 107.4(13) . . ?
C5M C13M C14M 130.5(13) . . ?
C5M C13M H13M 114.7 . . ?
C14M C13M H13M 114.7 . . ?
C19M C14M C15M 117.7 . . ?
C19M C14M C13M 115.1(11) . . ?
C15M C14M C13M 127.2(11) . . ?
C16M C15M C14M 121.0 . . ?
C16M C15M H15M 119.5 . . ?
C14M C15M H15M 119.5 . . ?
C17M C16M C15M 119.6 . . ?
C17M C16M H16M 120.1 . . ?
C15M C16M H16M 120.3 . . ?
C16M C17M C18M 119.9 . . ?
C16M C17M H17M 119.8 . . ?
C18M C17M H17M 120.2 . . ?
C19M C18M C17M 120.3 . . ?
C19M C18M H18M 119.8 . . ?
C17M C18M H18M 120.0 . . ?
C18M C19M C14M 121.5 . . ?
C18M C19M H19M 119.4 . . ?
C14M C19M H19M 119.1 . . ?
O1M C1D C2M 125.6(15) . . ?
O1M C1D C5D 127.8(17) . . ?
C2M C1D C5D 106.0(11) . . ?
C2M C3D C4D 104.4(16) . . ?
C2M C3D H3D1 110.9 . . ?
C4D C3D H3D1 110.9 . . ?
C2M C3D H3D2 110.9 . . ?
C4D C3D H3D2 110.9 . . ?
H3D1 C3D H3D2 108.9 . . ?
C5D C4D C3D 102.6(16) . . ?
C5D C4D H4D1 111.2 . . ?
C3D C4D H4D1 111.2 . . ?
C5D C4D H4D2 111.2 . . ?
C3D C4D H4D2 111.2 . . ?
H4D1 C4D H4D2 109.2 . . ?
C1D C5D C4D 104.0(14) . . ?
C1D C5D C13D 112.5(14) . . ?
C4D C5D C13D 122.0(17) . . ?
C1D C5D C13D 113.5(15) . 5_665 ?
C4D C5D C13D 112.8(18) . 5_665 ?
C13D C5D C13D 92.3(12) . 5_665 ?
C14D C13D C5D 124.2(16) . . ?
C14D C13D C5D 119.8(18) . 5_665 ?
C5D C13D C5D 87.7(12) . 5_665 ?
C14D C13D H13D 107.7 . . ?
C5D C13D H13D 107.7 . . ?
C5D C13D H13D 107.7 5_665 . ?
C19D C14D C15D 117.8 . . ?
C19D C14D C13D 123.5(13) . . ?
C15D C14D C13D 118.6(13) . . ?
C16D C15D C14D 120.7 . . ?
C16D C15D H15D 119.7 . . ?
C14D C15D H15D 119.6 . . ?
C17D C16D C15D 119.8 . . ?
C17D C16D H16D 120.2 . . ?
C15D C16D H16D 120.0 . . ?
C18D C17D C16D 120.0 . . ?
C18D C17D H17D 119.9 . . ?
C16D C17D H17D 120.1 . . ?
C17D C18D C19D 120.0 . . ?
C17D C18D H18D 120.1 . . ?
C19D C18D H18D 119.9 . . ?
C18D C19D C14D 121.7 . . ?
C18D C19D H19D 119.2 . . ?
C14D C19D H19D 119.1 . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.030

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_54.4%P_0.5GPa
_database_code_depnum_ccdc_archive 'CCDC 1491725'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_ATOM007_54.4%P_0.5GPa       
;
PROBLEM: atom_site_aniso_label is missing 
         Unique label identifying the atom site.

RESPONSE: The treatment of all atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
_vrf_RFACR01_54.4%P_0.5GPa       
;
PROBLEM: The value of the weighted R factor is > 0.45
         Weighted R factor given   0.450

RESPONSE: The high value of the weighted R factor is a consequence of the 
strong reactant-product disorder in the crystal and the high-pressure 
data collection.
;
_vrf_PLAT029_54.4%P_0.5GPa       
;
PROBLEM:  _diffrn_measured_fraction_theta_full value Low .      0.323 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_54.4%P_0.5GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         20 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================   
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   31.05(5)
_cell_length_b                   10.4910(16)
_cell_length_c                   8.5625(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2789(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    1062
_cell_measurement_theta_min      6.68
_cell_measurement_theta_max      23.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.56576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).

ABSORB-GUI - analytical corrections for the diamond-anvil cell 
[Angel R.J. & Gonzalez-Platas J. (2013). J. Appl. Cryst. 
46, 252-254].
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            11131
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_av_R_equivalents  0.2370
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.691
_diffrn_reflns_theta_max         24.463
_diffrn_reflns_theta_full        24.463
_diffrn_measured_fraction_theta_max 0.323
_diffrn_measured_fraction_theta_full 0.323
_diffrn_reflns_Laue_measured_fraction_max 0.323
_diffrn_reflns_Laue_measured_fraction_full 0.323
_diffrn_reflns_point_group_measured_fraction_max 0.323
_diffrn_reflns_point_group_measured_fraction_full 0.323
_reflns_number_total             743
_reflns_number_gt                331
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         743
_refine_ls_number_parameters     82
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2683
_refine_ls_R_factor_gt           0.1456
_refine_ls_wR_factor_ref         0.4502
_refine_ls_wR_factor_gt          0.3814
_refine_ls_goodness_of_fit_ref   1.411
_refine_ls_restrained_S_all      1.400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.4541(5) 0.7424(6) 0.0083(8) 0.095(3) Uiso 1 1 d D . . . .
C2M C 0.4152(6) 0.6223(9) 0.2022(14) 0.091(4) Uiso 1 1 d D . . . .
H2M H 0.4127 0.6711 0.2994 0.110 Uiso 1 1 calc R U . A 1
C6M C 0.3732(13) 0.6254(13) 0.1271(15) 0.106(5) Uiso 1 1 d . . . . .
H6M1 H 0.3690 0.7092 0.0817 0.127 Uiso 1 1 calc R U . . .
H6M2 H 0.3731 0.5640 0.0424 0.127 Uiso 1 1 calc R U . . .
C7M C 0.3378(5) 0.5984(9) 0.2282(11) 0.105(5) Uiso 1 1 d G . . . .
C8M C 0.3190(6) 0.4767(8) 0.2233(10) 0.121(5) Uiso 1 1 d G . . . .
H8M H 0.3308 0.4143 0.1549 0.145 Uiso 1 1 d G U . . .
C9M C 0.2840(6) 0.4443(8) 0.3143(14) 0.137(6) Uiso 1 1 d G . . . .
H9M H 0.2723 0.3603 0.3093 0.164 Uiso 1 1 d G U . . .
C10M C 0.2659(6) 0.5351(12) 0.4133(14) 0.193(9) Uiso 1 1 d G . . . .
H10M H 0.2417 0.5132 0.4757 0.231 Uiso 1 1 d G U . . .
C11M C 0.2834(6) 0.6598(10) 0.4216(13) 0.154(7) Uiso 1 1 d G . . . .
H11M H 0.2709 0.7223 0.4885 0.185 Uiso 1 1 d G U . . .
C12M C 0.3196(6) 0.6896(7) 0.3293(13) 0.126(5) Uiso 1 1 d G . . . .
H12M H 0.3318 0.7727 0.3354 0.152 Uiso 1 1 d G U . . .
C1M C 0.4543(8) 0.6699(18) 0.120(2) 0.071(4) Uiso 0.456(11) 1 d D U P B 1
C3M C 0.4293(10) 0.4869(16) 0.247(3) 0.071(4) Uiso 0.456(11) 1 d D U P B 1
H3M1 H 0.4195 0.4261 0.1694 0.085 Uiso 0.456(11) 1 calc R U P B 1
H3M2 H 0.4173 0.4633 0.3475 0.085 Uiso 0.456(11) 1 calc R U P B 1
C4M C 0.4788(10) 0.487(2) 0.255(3) 0.071(4) Uiso 0.456(11) 1 d D U P B 1
H4M1 H 0.4884 0.4889 0.3631 0.085 Uiso 0.456(11) 1 calc R U P B 1
H4M2 H 0.4905 0.4119 0.2053 0.085 Uiso 0.456(11) 1 calc R U P B 1
C5M C 0.4933(8) 0.6037(18) 0.173(2) 0.071(4) Uiso 0.456(11) 1 d D U P B 1
C13M C 0.5317(9) 0.652(2) 0.129(3) 0.071(4) Uiso 0.456(11) 1 d D U P B 1
H13M H 0.5290 0.7164 0.0552 0.085 Uiso 0.456(11) 1 calc R U P B 1
C14M C 0.5758(9) 0.6261(19) 0.169(2) 0.074(8) Uiso 0.456(11) 1 d DG U P B 1
C15M C 0.5902(10) 0.5372(17) 0.283(2) 0.099(10) Uiso 0.456(11) 1 d DG U P B 1
H15M H 0.5698 0.4859 0.3361 0.118 Uiso 0.456(11) 1 d G U P B 1
C16M C 0.6346(11) 0.5240(18) 0.317(2) 0.078(7) Uiso 0.456(11) 1 d G U P B 1
H16M H 0.6440 0.4637 0.3933 0.094 Uiso 0.456(11) 1 d G U P B 1
C17M C 0.6647(10) 0.600(2) 0.239(3) 0.123(11) Uiso 0.456(11) 1 d G U P B 1
H17M H 0.6946 0.5925 0.2637 0.148 Uiso 0.456(11) 1 d G U P B 1
C18M C 0.6509(10) 0.687(2) 0.126(3) 0.097(8) Uiso 0.456(11) 1 d G U P B 1
H18M H 0.6713 0.7380 0.0724 0.116 Uiso 0.456(11) 1 d G U P B 1
C19M C 0.6071(10) 0.6977(18) 0.090(2) 0.090(10) Uiso 0.456(11) 1 d DG U P B 1
H19M H 0.5982 0.7552 0.0100 0.109 Uiso 0.456(11) 1 d G U P B 1
C1D C 0.4503(7) 0.6445(13) 0.0891(16) 0.058(3) Uiso 0.544(11) 1 d D U P B 2
C3D C 0.4297(10) 0.5010(15) 0.2907(19) 0.058(3) Uiso 0.544(11) 1 d D U P B 2
H3D1 H 0.4208 0.5036 0.3992 0.070 Uiso 0.544(11) 1 calc R U P B 2
H3D2 H 0.4183 0.4247 0.2422 0.070 Uiso 0.544(11) 1 calc R U P B 2
C4D C 0.4792(10) 0.507(2) 0.2756(17) 0.058(3) Uiso 0.544(11) 1 d D U P B 2
H4D1 H 0.4916 0.5739 0.3398 0.070 Uiso 0.544(11) 1 calc R U P B 2
H4D2 H 0.4927 0.4262 0.3007 0.070 Uiso 0.544(11) 1 calc R U P B 2
C5D C 0.4823(6) 0.5381(12) 0.1008(12) 0.058(3) Uiso 0.544(11) 1 d D U P B 2
C13D C 0.5259(5) 0.5710(12) 0.0268(15) 0.058(3) Uiso 0.544(11) 1 d D U P B 2
H13D H 0.5224 0.6530 -0.0265 0.070 Uiso 0.544(11) 1 calc R U P B 2
C14D C 0.5670(6) 0.5782(16) 0.1170(17) 0.076(7) Uiso 0.544(11) 1 d DG U P B 2
C15D C 0.5774(7) 0.4868(14) 0.2333(17) 0.085(7) Uiso 0.544(11) 1 d DG U P B 2
H15D H 0.5570 0.4222 0.2594 0.102 Uiso 0.544(11) 1 d G U P B 2
C16D C 0.6176(8) 0.4907(16) 0.311(2) 0.094(7) Uiso 0.544(11) 1 d G U P B 2
H16D H 0.6243 0.4287 0.3880 0.112 Uiso 0.544(11) 1 d G U P B 2
C17D C 0.6475(7) 0.586(2) 0.273(3) 0.125(10) Uiso 0.544(11) 1 d G U P B 2
H17D H 0.6744 0.5901 0.3264 0.150 Uiso 0.544(11) 1 d G U P B 2
C18D C 0.6378(7) 0.6756(17) 0.158(2) 0.081(6) Uiso 0.544(11) 1 d G U P B 2
H18D H 0.6581 0.7403 0.1318 0.097 Uiso 0.544(11) 1 d G U P B 2
C19D C 0.5983(7) 0.6700(15) 0.0794(17) 0.098(9) Uiso 0.544(11) 1 d DG U P B 2
H19D H 0.5925 0.7299 -0.0011 0.118 Uiso 0.544(11) 1 d G U P B 2

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1M 1.219(14) . ?
O1M C1D 1.244(12) . ?
C2M C6M 1.45(4) . ?
C2M C1D 1.476(17) . ?
C2M C1M 1.492(17) . ?
C2M C3M 1.536(17) . ?
C2M C3D 1.548(16) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.43(3) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.4052 . ?
C7M C12M 1.4100 . ?
C8M C9M 1.3802 . ?
C8M H8M 0.9519 . ?
C9M C10M 1.3938 . ?
C9M H9M 0.9532 . ?
C10M C11M 1.4185 . ?
C10M H10M 0.9508 . ?
C11M C12M 1.4092 . ?
C11M H11M 0.9519 . ?
C12M H12M 0.9525 . ?
C1M C5M 1.467(17) . ?
C3M C4M 1.54(2) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.480(17) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.347(17) . ?
C13M C14M 1.438(17) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.4011 . ?
C14M C15M 1.4222 . ?
C15M C16M 1.4174 . ?
C15M H15M 0.9493 . ?
C16M C17M 1.3983 . ?
C16M H16M 0.9522 . ?
C17M C18M 1.4000 . ?
C17M H17M 0.9525 . ?
C18M C19M 1.4003 . ?
C18M H18M 0.9478 . ?
C19M H19M 0.9517 . ?
C1D C5D 1.497(16) . ?
C3D C4D 1.544(19) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.534(14) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.535(16) . ?
C5D C13D 1.603(12) 5_665 ?
C13D C14D 1.493(15) . ?
C13D C5D 1.603(12) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.4059 . ?
C14D C15D 1.4195 . ?
C15D C16D 1.4160 . ?
C15D H15D 0.9525 . ?
C16D C17D 1.4028 . ?
C16D H16D 0.9505 . ?
C17D C18D 1.3975 . ?
C17D H17D 0.9516 . ?
C18D C19D 1.3987 . ?
C18D H18D 0.9509 . ?
C19D H19D 0.9501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6M C2M C1D 111.6(13) . . ?
C6M C2M C1M 120.9(13) . . ?
C6M C2M C3M 112.8(15) . . ?
C1M C2M C3M 101.3(14) . . ?
C6M C2M C3D 119.7(15) . . ?
C1D C2M C3D 103.6(13) . . ?
C6M C2M H2M 107.0 . . ?
C1M C2M H2M 107.0 . . ?
C3M C2M H2M 107.0 . . ?
C7M C6M C2M 114.7(10) . . ?
C7M C6M H6M1 108.6 . . ?
C2M C6M H6M1 108.6 . . ?
C7M C6M H6M2 108.6 . . ?
C2M C6M H6M2 108.6 . . ?
H6M1 C6M H6M2 107.6 . . ?
C8M C7M C12M 117.9 . . ?
C8M C7M C6M 118.9(10) . . ?
C12M C7M C6M 123.2(10) . . ?
C9M C8M C7M 122.4 . . ?
C9M C8M H8M 118.7 . . ?
C7M C8M H8M 118.9 . . ?
C8M C9M C10M 119.5 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.4 . . ?
C9M C10M C11M 120.5 . . ?
C9M C10M H10M 119.7 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.6 . . ?
C10M C11M H11M 120.6 . . ?
C11M C12M C7M 121.0 . . ?
C11M C12M H12M 119.4 . . ?
C7M C12M H12M 119.6 . . ?
O1M C1M C5M 122.9(17) . . ?
O1M C1M C2M 125.0(18) . . ?
C5M C1M C2M 111.5(12) . . ?
C2M C3M C4M 107.1(16) . . ?
C2M C3M H3M1 110.3 . . ?
C4M C3M H3M1 110.3 . . ?
C2M C3M H3M2 110.3 . . ?
C4M C3M H3M2 110.3 . . ?
H3M1 C3M H3M2 108.6 . . ?
C5M C4M C3M 106.5(16) . . ?
C5M C4M H4M1 110.4 . . ?
C3M C4M H4M1 110.4 . . ?
C5M C4M H4M2 110.4 . . ?
C3M C4M H4M2 110.4 . . ?
H4M1 C4M H4M2 108.6 . . ?
C13M C5M C1M 117.8(16) . . ?
C13M C5M C4M 135.2(18) . . ?
C1M C5M C4M 106.8(15) . . ?
C5M C13M C14M 135.0(18) . . ?
C5M C13M H13M 112.5 . . ?
C14M C13M H13M 112.5 . . ?
C19M C14M C15M 117.7 . . ?
C19M C14M C13M 116.4(15) . . ?
C15M C14M C13M 125.9(15) . . ?
C16M C15M C14M 121.0 . . ?
C16M C15M H15M 119.5 . . ?
C14M C15M H15M 119.5 . . ?
C17M C16M C15M 119.6 . . ?
C17M C16M H16M 120.1 . . ?
C15M C16M H16M 120.3 . . ?
C16M C17M C18M 119.9 . . ?
C16M C17M H17M 119.9 . . ?
C18M C17M H17M 120.2 . . ?
C17M C18M C19M 120.3 . . ?
C17M C18M H18M 119.9 . . ?
C19M C18M H18M 119.8 . . ?
C18M C19M C14M 121.6 . . ?
C18M C19M H19M 119.4 . . ?
C14M C19M H19M 119.0 . . ?
O1M C1D C2M 124.4(13) . . ?
O1M C1D C5D 126.2(15) . . ?
C2M C1D C5D 109.1(10) . . ?
C4D C3D C2M 102.5(14) . . ?
C4D C3D H3D1 111.3 . . ?
C2M C3D H3D1 111.3 . . ?
C4D C3D H3D2 111.3 . . ?
C2M C3D H3D2 111.3 . . ?
H3D1 C3D H3D2 109.2 . . ?
C5D C4D C3D 98.7(14) . . ?
C5D C4D H4D1 112.0 . . ?
C3D C4D H4D1 112.0 . . ?
C5D C4D H4D2 112.0 . . ?
C3D C4D H4D2 112.0 . . ?
H4D1 C4D H4D2 109.7 . . ?
C1D C5D C4D 100.5(11) . . ?
C1D C5D C13D 113.0(12) . . ?
C4D C5D C13D 120.3(15) . . ?
C1D C5D C13D 112.4(13) . 5_665 ?
C4D C5D C13D 120.2(13) . 5_665 ?
C13D C5D C13D 91.1(10) . 5_665 ?
C14D C13D C5D 123.5(12) . . ?
C14D C13D C5D 121.7(15) . 5_665 ?
C5D C13D C5D 88.9(10) . 5_665 ?
C14D C13D H13D 106.9 . . ?
C5D C13D H13D 106.9 . . ?
C5D C13D H13D 106.9 5_665 . ?
C19D C14D C15D 117.8 . . ?
C19D C14D C13D 120.5(11) . . ?
C15D C14D C13D 121.5(11) . . ?
C16D C15D C14D 120.6 . . ?
C16D C15D H15D 119.7 . . ?
C14D C15D H15D 119.6 . . ?
C17D C16D C15D 119.8 . . ?
C17D C16D H16D 120.2 . . ?
C15D C16D H16D 120.0 . . ?
C18D C17D C16D 120.0 . . ?
C18D C17D H17D 119.9 . . ?
C16D C17D H17D 120.1 . . ?
C17D C18D C19D 119.9 . . ?
C17D C18D H18D 120.1 . . ?
C19D C18D H18D 120.0 . . ?
C18D C19D C14D 121.7 . . ?
C18D C19D H19D 119.1 . . ?
C14D C19D H19D 119.1 . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_80.1%P_0.5GPa
_database_code_depnum_ccdc_archive 'CCDC 1491726'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_80.1%P_0.5GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.327 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_80.1%P_0.5GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================    
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.99(3)
_cell_length_b                   10.5162(12)
_cell_length_c                   8.5388(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2783(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    1231
_cell_measurement_theta_min      6.67
_cell_measurement_theta_max      21.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.58370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).

ABSORB-GUI - analytical corrections for the diamond-anvil cell 
[Angel R.J. & Gonzalez-Platas J. (2013). J. Appl. Cryst. 
46, 252-254].
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            11099
_diffrn_reflns_av_unetI/netI     0.1199
_diffrn_reflns_av_R_equivalents  0.2381
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.697
_diffrn_reflns_theta_max         24.467
_diffrn_reflns_theta_full        24.467
_diffrn_measured_fraction_theta_max 0.327
_diffrn_measured_fraction_theta_full 0.327
_diffrn_reflns_Laue_measured_fraction_max 0.327
_diffrn_reflns_Laue_measured_fraction_full 0.327
_diffrn_reflns_point_group_measured_fraction_max 0.327
_diffrn_reflns_point_group_measured_fraction_full 0.327
_reflns_number_total             751
_reflns_number_gt                372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinemen
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1843P)²+4.0928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         751
_refine_ls_number_parameters     87
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.2247
_refine_ls_R_factor_gt           0.1203
_refine_ls_wR_factor_ref         0.3732
_refine_ls_wR_factor_gt          0.3024
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.4513(5) 0.7390(6) 0.0134(8) 0.086(13) Uani 1 1 d D . . . .
C2M C 0.4156(6) 0.6209(9) 0.2138(13) 0.080(4) Uiso 1 1 d D . . . .
H2M H 0.4155 0.6789 0.3037 0.096 Uiso 1 1 calc R U . A 1
C6M C 0.3714(12) 0.6247(12) 0.1354(14) 0.097(4) Uiso 1 1 d . . . . .
H6M1 H 0.3667 0.7090 0.0924 0.116 Uiso 1 1 calc R U . . .
H6M2 H 0.3711 0.5648 0.0490 0.116 Uiso 1 1 calc R U . . .
C7M C 0.3352(6) 0.5937(8) 0.2429(10) 0.087(4) Uiso 1 1 d G . . . .
C8M C 0.3168(6) 0.4715(7) 0.2388(11) 0.108(5) Uiso 1 1 d G . . . .
H8M H 0.3282 0.4099 0.1684 0.129 Uiso 1 1 d G U . . .
C9M C 0.2826(6) 0.4375(8) 0.3331(14) 0.135(6) Uiso 1 1 d G . . . .
H9M H 0.2712 0.3532 0.3285 0.162 Uiso 1 1 d G U . . .
C10M C 0.2650(6) 0.5271(11) 0.4350(13) 0.150(7) Uiso 1 1 d G . . . .
H10M H 0.2414 0.5041 0.4997 0.180 Uiso 1 1 d G U . . .
C11M C 0.2822(6) 0.6523(9) 0.4427(12) 0.130(6) Uiso 1 1 d G . . . .
H11M H 0.2700 0.7139 0.5116 0.156 Uiso 1 1 d G U . . .
C12M C 0.3175(6) 0.6838(7) 0.3469(12) 0.109(5) Uiso 1 1 d G . . . .
H12M H 0.3295 0.7672 0.3526 0.130 Uiso 1 1 d G U . . .
C1M C 0.4529(10) 0.655(6) 0.107(6) 0.069(7) Uiso 0.199(13) 1 d D U P B 1
C3M C 0.4314(14) 0.489(3) 0.268(7) 0.069(7) Uiso 0.199(13) 1 d D U P B 1
H3M1 H 0.4271 0.4255 0.1872 0.083 Uiso 0.199(13) 1 calc R U P B 1
H3M2 H 0.4168 0.4623 0.3628 0.083 Uiso 0.199(13) 1 calc R U P B 1
C4M C 0.4798(14) 0.513(5) 0.298(5) 0.069(7) Uiso 0.199(13) 1 d D U P B 1
H4M1 H 0.4844 0.5476 0.4020 0.083 Uiso 0.199(13) 1 calc R U P B 1
H4M2 H 0.4961 0.4343 0.2886 0.083 Uiso 0.199(13) 1 calc R U P B 1
C5M C 0.4931(10) 0.605(4) 0.176(5) 0.069(7) Uiso 0.199(13) 1 d D U P B 1
C13M C 0.5309(12) 0.657(4) 0.135(5) 0.069(7) Uiso 0.199(13) 1 d D U P B 1
H13M H 0.5273 0.7302 0.0747 0.083 Uiso 0.199(13) 1 calc R U P B 1
C14M C 0.5757(13) 0.628(4) 0.161(5) 0.080(15) Uiso 0.199(13) 1 d DG U P B 1
C15M C 0.5934(15) 0.542(4) 0.273(4) 0.077(10) Uiso 0.199(13) 1 d DG U P B 1
H15M H 0.5748 0.4880 0.3302 0.093 Uiso 0.199(13) 1 d G U P B 1
C16M C 0.6385(16) 0.536(4) 0.298(4) 0.050(9) Uiso 0.199(13) 1 d G U P B 1
H16M H 0.6500 0.4775 0.3724 0.060 Uiso 0.199(13) 1 d G U P B 1
C17M C 0.6659(13) 0.616(4) 0.214(5) 0.085(10) Uiso 0.199(13) 1 d G U P B 1
H17M H 0.6962 0.6133 0.2322 0.102 Uiso 0.199(13) 1 d G U P B 1
C18M C 0.6489(14) 0.700(4) 0.103(5) 0.093(10) Uiso 0.199(13) 1 d G U P B 1
H18M H 0.6675 0.7542 0.0454 0.111 Uiso 0.199(13) 1 d G U P B 1
C19M C 0.6044(14) 0.704(4) 0.076(4) 0.082(16) Uiso 0.199(13) 1 d DG U P B 1
H19M H 0.5933 0.7598 -0.0021 0.098 Uiso 0.199(13) 1 d G U P B 1
C1D C 0.4505(7) 0.6466(14) 0.0972(17) 0.060(2) Uiso 0.801(13) 1 d D U P B 2
C3D C 0.4292(7) 0.4975(11) 0.2948(17) 0.060(2) Uiso 0.801(13) 1 d D U P B 2
H3D1 H 0.4151 0.4246 0.2476 0.073 Uiso 0.801(13) 1 calc R U P B 2
H3D2 H 0.4223 0.4998 0.4056 0.073 Uiso 0.801(13) 1 calc R U P B 2
C4D C 0.4784(7) 0.4925(13) 0.2693(13) 0.060(2) Uiso 0.801(13) 1 d D U P B 2
H4D1 H 0.4934 0.5490 0.3407 0.073 Uiso 0.801(13) 1 calc R U P B 2
H4D2 H 0.4894 0.4068 0.2820 0.073 Uiso 0.801(13) 1 calc R U P B 2
C5D C 0.4825(5) 0.5372(9) 0.1013(10) 0.060(2) Uiso 0.801(13) 1 d D U P B 2
C13D C 0.5258(5) 0.5720(9) 0.0235(12) 0.060(2) Uiso 0.801(13) 1 d D U P B 2
H13D H 0.5215 0.6533 -0.0305 0.073 Uiso 0.801(13) 1 calc R U P B 2
C14D C 0.5669(5) 0.5824(10) 0.1129(11) 0.061(4) Uiso 0.801(13) 1 d DG U P B 2
C15D C 0.5791(5) 0.4924(9) 0.2286(11) 0.076(5) Uiso 0.801(13) 1 d DG U P B 2
H15D H 0.5593 0.4278 0.2595 0.092 Uiso 0.801(13) 1 d G U P B 2
C16D C 0.6204(5) 0.4976(9) 0.2983(12) 0.078(5) Uiso 0.801(13) 1 d G U P B 2
H16D H 0.6283 0.4366 0.3751 0.094 Uiso 0.801(13) 1 d G U P B 2
C17D C 0.6496(5) 0.5930(12) 0.2534(16) 0.100(5) Uiso 0.801(13) 1 d G U P B 2
H17D H 0.6772 0.5979 0.3013 0.120 Uiso 0.801(13) 1 d G U P B 2
C18D C 0.6381(5) 0.6811(10) 0.1382(14) 0.079(5) Uiso 0.801(13) 1 d G U P B 2
H18D H 0.6578 0.7457 0.1077 0.095 Uiso 0.801(13) 1 d G U P B 2
C19D C 0.5975(5) 0.6741(9) 0.0679(10) 0.081(5) Uiso 0.801(13) 1 d DG U P B 2
H19D H 0.5904 0.7330 -0.0124 0.097 Uiso 0.801(13) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1M 1.194(17) . ?
O1M C1D 1.208(10) . ?
C2M C1D 1.494(16) . ?
C2M C1M 1.51(2) . ?
C2M C6M 1.53(4) . ?
C2M C3D 1.530(14) . ?
C2M C3M 1.54(2) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.48(3) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.4074 . ?
C7M C12M 1.4097 . ?
C8M C9M 1.3775 . ?
C8M H8M 0.9518 . ?
C9M C10M 1.3936 . ?
C9M H9M 0.9548 . ?
C10M C11M 1.4210 . ?
C10M H10M 0.9489 . ?
C11M C12M 1.4064 . ?
C11M H11M 0.9518 . ?
C12M H12M 0.9541 . ?
C1M C5M 1.475(18) . ?
C3M C4M 1.54(2) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.486(19) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.337(18) . ?
C13M C14M 1.441(17) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.4000 . ?
C14M C15M 1.4217 . ?
C15M C16M 1.4147 . ?
C15M H15M 0.9488 . ?
C16M C17M 1.3975 . ?
C16M H16M 0.9518 . ?
C17M C18M 1.3994 . ?
C17M H17M 0.9506 . ?
C18M C19M 1.3976 . ?
C18M H18M 0.9472 . ?
C19M H19M 0.9511 . ?
C1D C5D 1.519(15) . ?
C3D C4D 1.540(19) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.515(13) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.541(15) . ?
C5D C13D 1.587(11) 5_665 ?
C13D C14D 1.490(14) . ?
C13D C5D 1.587(11) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.4060 . ?
C14D C15D 1.4191 . ?
C15D C16D 1.4130 . ?
C15D H15D 0.9528 . ?
C16D C17D 1.4030 . ?
C16D H16D 0.9501 . ?
C17D C18D 1.3969 . ?
C17D H17D 0.9496 . ?
C18D C19D 1.3957 . ?
C18D H18D 0.9511 . ?
C19D H19D 0.9496 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1D C2M C6M 110.7(12) . . ?
C1M C2M C6M 115(2) . . ?
C1D C2M C3D 104.7(12) . . ?
C6M C2M C3D 117.9(13) . . ?
C1M C2M C3M 98.7(18) . . ?
C6M C2M C3M 116(2) . . ?
C1M C2M H2M 109.0 . . ?
C6M C2M H2M 109.0 . . ?
C3M C2M H2M 109.0 . . ?
C7M C6M C2M 113.6(10) . . ?
C7M C6M H6M1 108.8 . . ?
C2M C6M H6M1 108.8 . . ?
C7M C6M H6M2 108.8 . . ?
C2M C6M H6M2 108.8 . . ?
H6M1 C6M H6M2 107.7 . . ?
C8M C7M C12M 118.1 . . ?
C8M C7M C6M 119.4(8) . . ?
C12M C7M C6M 122.5(8) . . ?
C9M C8M C7M 122.3 . . ?
C9M C8M H8M 118.6 . . ?
C7M C8M H8M 119.1 . . ?
C8M C9M C10M 119.3 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.5 . . ?
C9M C10M C11M 120.6 . . ?
C9M C10M H10M 119.5 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.4 . . ?
C10M C11M H11M 120.8 . . ?
C11M C12M C7M 120.8 . . ?
C11M C12M H12M 119.4 . . ?
C7M C12M H12M 119.8 . . ?
O1M C1M C5M 124(2) . . ?
O1M C1M C2M 123(2) . . ?
C5M C1M C2M 109(2) . . ?
C2M C3M C4M 102(2) . . ?
C2M C3M H3M1 111.3 . . ?
C4M C3M H3M1 111.3 . . ?
C2M C3M H3M2 111.3 . . ?
C4M C3M H3M2 111.3 . . ?
H3M1 C3M H3M2 109.2 . . ?
C5M C4M C3M 105.0(19) . . ?
C5M C4M H4M1 110.8 . . ?
C3M C4M H4M1 110.8 . . ?
C5M C4M H4M2 110.8 . . ?
C3M C4M H4M2 110.8 . . ?
H4M1 C4M H4M2 108.8 . . ?
C13M C5M C1M 119(2) . . ?
C13M C5M C4M 134(2) . . ?
C1M C5M C4M 106.1(16) . . ?
C5M C13M C14M 136(3) . . ?
C5M C13M H13M 112.1 . . ?
C14M C13M H13M 112.1 . . ?
C19M C14M C15M 117.8 . . ?
C19M C14M C13M 114(2) . . ?
C15M C14M C13M 128(2) . . ?
C16M C15M C14M 120.9 . . ?
C16M C15M H15M 119.5 . . ?
C14M C15M H15M 119.6 . . ?
C17M C16M C15M 119.5 . . ?
C17M C16M H16M 120.2 . . ?
C15M C16M H16M 120.3 . . ?
C16M C17M C18M 120.0 . . ?
C16M C17M H17M 119.8 . . ?
C18M C17M H17M 120.2 . . ?
C19M C18M C17M 120.2 . . ?
C19M C18M H18M 119.8 . . ?
C17M C18M H18M 120.0 . . ?
C18M C19M C14M 121.5 . . ?
C18M C19M H19M 119.4 . . ?
C14M C19M H19M 119.1 . . ?
O1M C1D C2M 123.7(13) . . ?
O1M C1D C5D 127.5(13) . . ?
C2M C1D C5D 108.7(9) . . ?
C2M C3D C4D 103.8(12) . . ?
C2M C3D H3D1 111.0 . . ?
C4D C3D H3D1 111.0 . . ?
C2M C3D H3D2 111.0 . . ?
C4D C3D H3D2 111.0 . . ?
H3D1 C3D H3D2 109.0 . . ?
C5D C4D C3D 101.9(12) . . ?
C5D C4D H4D1 111.4 . . ?
C3D C4D H4D1 111.4 . . ?
C5D C4D H4D2 111.4 . . ?
C3D C4D H4D2 111.4 . . ?
H4D1 C4D H4D2 109.2 . . ?
C4D C5D C1D 101.6(10) . . ?
C4D C5D C13D 123.7(13) . . ?
C1D C5D C13D 112.2(10) . . ?
C4D C5D C13D 113.5(9) . 5_665 ?
C1D C5D C13D 115.3(12) . 5_665 ?
C13D C5D C13D 91.3(9) . 5_665 ?
C14D C13D C5D 122.8(9) . . ?
C14D C13D C5D 122.3(12) . 5_665 ?
C5D C13D C5D 88.7(9) . 5_665 ?
C14D C13D H13D 107.0 . . ?
C5D C13D H13D 107.0 . . ?
C5D C13D H13D 107.0 5_665 . ?
C19D C14D C15D 117.9 . . ?
C19D C14D C13D 119.1(7) . . ?
C15D C14D C13D 122.4(7) . . ?
C16D C15D C14D 120.5 . . ?
C16D C15D H15D 119.7 . . ?
C14D C15D H15D 119.8 . . ?
C17D C16D C15D 119.8 . . ?
C17D C16D H16D 120.4 . . ?
C15D C16D H16D 119.9 . . ?
C18D C17D C16D 120.1 . . ?
C18D C17D H17D 119.8 . . ?
C16D C17D H17D 120.0 . . ?
C19D C18D C17D 119.9 . . ?
C19D C18D H18D 120.0 . . ?
C17D C18D H18D 120.2 . . ?
C18D C19D C14D 121.7 . . ?
C18D C19D H19D 119.0 . . ?
C14D C19D H19D 119.3 . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.035

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_100%P_0.5GPa
_database_code_depnum_ccdc_archive 'CCDC 1491727'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_100%P_0.5GPa        
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.332 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_100%P_0.5GPa        
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================     
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.83(3)
_cell_length_b                   10.5572(11)
_cell_length_c                   8.5066(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2769(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    1468
_cell_measurement_theta_min      6.59
_cell_measurement_theta_max      22.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.09187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            11251
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.1604
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.707
_diffrn_reflns_theta_max         24.417
_diffrn_reflns_theta_full        24.417
_diffrn_measured_fraction_theta_max 0.332
_diffrn_measured_fraction_theta_full 0.332
_diffrn_reflns_Laue_measured_fraction_max 0.332
_diffrn_reflns_Laue_measured_fraction_full 0.332
_diffrn_reflns_point_group_measured_fraction_max 0.332
_diffrn_reflns_point_group_measured_fraction_full 0.332
_reflns_number_total             757
_reflns_number_gt                429
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1415P)²+6.0651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         757
_refine_ls_number_parameters     92
_refine_ls_number_restraints     110
_refine_ls_R_factor_all          0.1812
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.3041
_refine_ls_wR_factor_gt          0.2518
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1D O 0.4507(5) 0.7366(5) 0.0205(6) 0.083(11) Uani 1 1 d . . . . .
C1D C 0.4496(8) 0.6420(7) 0.1014(9) 0.045(2) Uiso 1 1 d . . . . .
C2D C 0.4172(10) 0.6182(8) 0.2187(12) 0.068(3) Uiso 1 1 d . . . . .
H2D H 0.4192 0.6861 0.2970 0.082 Uiso 1 1 calc R U . . .
C3D C 0.4291(11) 0.4950(8) 0.3005(12) 0.061(4) Uiso 1 1 d . . . . .
H3D1 H 0.4150 0.4229 0.2517 0.073 Uiso 1 1 calc R U . . .
H3D2 H 0.4218 0.4973 0.4113 0.073 Uiso 1 1 calc R U . . .
C4D C 0.4782(11) 0.4917(8) 0.2755(10) 0.054(3) Uiso 1 1 d . . . . .
H4D1 H 0.4896 0.4068 0.2880 0.065 Uiso 1 1 calc R U . . .
H4D2 H 0.4930 0.5486 0.3471 0.065 Uiso 1 1 calc R U . . .
C5D C 0.4818(7) 0.5372(7) 0.1046(9) 0.048(2) Uiso 1 1 d . . . . .
C6D C 0.3686(11) 0.6218(10) 0.1460(13) 0.081(4) Uiso 1 1 d . . . . .
H6D1 H 0.3632 0.7060 0.1045 0.097 Uiso 1 1 calc R U . . .
H6D2 H 0.3671 0.5628 0.0588 0.097 Uiso 1 1 calc R U . . .
C7D C 0.3353(5) 0.5915(7) 0.2547(9) 0.075(3) Uiso 1 1 d G . . . .
C8D C 0.3172(5) 0.4690(6) 0.2516(10) 0.092(4) Uiso 1 1 d G U . . .
H8D H 0.3288 0.4074 0.1814 0.110 Uiso 1 1 d G U . . .
C9D C 0.2831(5) 0.4346(8) 0.3469(13) 0.116(8) Uani 1 1 d G U . . .
H9D H 0.2719 0.3502 0.3430 0.139 Uiso 1 1 d G U . . .
C10D C 0.2653(5) 0.5242(12) 0.4486(12) 0.123(8) Uani 1 1 d G U . . .
H10D H 0.2417 0.5010 0.5140 0.147 Uiso 1 1 d G U . . .
C11D C 0.2821(6) 0.6497(10) 0.4552(11) 0.112(8) Uani 1 1 d G U . . .
H11D H 0.2698 0.7113 0.5239 0.134 Uiso 1 1 d G U . . .
C12D C 0.3173(6) 0.6816(6) 0.3585(11) 0.093(4) Uiso 1 1 d G U . . .
H12D H 0.3292 0.7652 0.3634 0.111 Uiso 1 1 d G U . . .
C13D C 0.5262(8) 0.5713(7) 0.0228(9) 0.045(2) Uiso 1 1 d . . . . .
H13D H 0.5217 0.6521 -0.0315 0.054 Uiso 1 1 calc R U . . .
C14D C 0.5674(4) 0.5829(6) 0.1076(7) 0.050(2) Uiso 1 1 d G . . . .
C15D C 0.5814(5) 0.4946(5) 0.2230(8) 0.068(3) Uiso 1 1 d G U . . .
H15D H 0.5624 0.4290 0.2572 0.081 Uiso 1 1 d G U . . .
C16D C 0.6233(5) 0.5031(7) 0.2876(7) 0.076(7) Uani 1 1 d G U . . .
H16D H 0.6325 0.4431 0.3643 0.091 Uiso 1 1 d G U . . .
C17D C 0.6513(4) 0.6000(9) 0.2380(10) 0.091(7) Uani 1 1 d G U . . .
H17D H 0.6793 0.6071 0.2826 0.110 Uiso 1 1 d G U . . .
C18D C 0.6380(4) 0.6865(7) 0.1230(10) 0.082(7) Uani 1 1 d G U . . .
H18D H 0.6569 0.7522 0.0892 0.098 Uiso 1 1 d G U . . .
C19D C 0.5968(5) 0.6763(5) 0.0576(7) 0.070(4) Uiso 1 1 d G U . . .
H19D H 0.5884 0.7342 -0.0227 0.084 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1D C1D 1.213(9) . ?
C1D C2D 1.43(3) . ?
C1D C5D 1.49(2) . ?
C2D C3D 1.520(17) . ?
C2D C6D 1.62(4) . ?
C2D H2D 0.9800 . ?
C3D C4D 1.53(4) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.536(13) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.58(3) . ?
C5D C13D 1.596(12) 5_665 ?
C6D C7D 1.42(3) . ?
C6D H6D1 0.9700 . ?
C6D H6D2 0.9700 . ?
C7D C8D 1.4102 . ?
C7D C12D 1.4109 . ?
C8D C9D 1.3757 . ?
C8D H8D 0.9527 . ?
C9D C10D 1.3948 . ?
C9D H9D 0.9569 . ?
C10D C11D 1.4240 . ?
C10D H10D 0.9476 . ?
C11D C12D 1.4045 . ?
C11D H11D 0.9525 . ?
C12D H12D 0.9560 . ?
C13D C14D 1.46(2) . ?
C13D C5D 1.596(12) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.4051 . ?
C14D C15D 1.4214 . ?
C15D C16D 1.4074 . ?
C15D H15D 0.9526 . ?
C16D C17D 1.4029 . ?
C16D H16D 0.9518 . ?
C17D C18D 1.3993 . ?
C17D H17D 0.9459 . ?
C18D C19D 1.3905 . ?
C18D H18D 0.9509 . ?
C19D H19D 0.9514 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1D C1D C2D 123.9(15) . . ?
O1D C1D C5D 127.2(16) . . ?
C2D C1D C5D 108.8(10) . . ?
C1D C2D C3D 107(2) . . ?
C1D C2D C6D 112.0(10) . . ?
C3D C2D C6D 114.8(19) . . ?
C1D C2D H2D 107.4 . . ?
C3D C2D H2D 107.4 . . ?
C6D C2D H2D 107.4 . . ?
C2D C3D C4D 101.3(18) . . ?
C2D C3D H3D1 111.5 . . ?
C4D C3D H3D1 111.5 . . ?
C2D C3D H3D2 111.5 . . ?
C4D C3D H3D2 111.5 . . ?
H3D1 C3D H3D2 109.3 . . ?
C3D C4D C5D 101.3(18) . . ?
C3D C4D H4D1 111.5 . . ?
C5D C4D H4D1 111.5 . . ?
C3D C4D H4D2 111.5 . . ?
C5D C4D H4D2 111.5 . . ?
H4D1 C4D H4D2 109.3 . . ?
C1D C5D C4D 101.6(13) . . ?
C1D C5D C13D 113.7(10) . . ?
C4D C5D C13D 123.4(19) . . ?
C1D C5D C13D 114.8(14) . 5_665 ?
C4D C5D C13D 114.0(8) . 5_665 ?
C13D C5D C13D 89.9(12) . 5_665 ?
C7D C6D C2D 114.5(10) . . ?
C7D C6D H6D1 108.6 . . ?
C2D C6D H6D1 108.6 . . ?
C7D C6D H6D2 108.6 . . ?
C2D C6D H6D2 108.6 . . ?
H6D1 C6D H6D2 107.6 . . ?
C8D C7D C12D 118.3 . . ?
C8D C7D C6D 118.8(8) . . ?
C12D C7D C6D 122.7(8) . . ?
C9D C8D C7D 122.3 . . ?
C9D C8D H8D 118.4 . . ?
C7D C8D H8D 119.3 . . ?
C8D C9D C10D 119.2 . . ?
C8D C9D H9D 120.1 . . ?
C10D C9D H9D 120.7 . . ?
C9D C10D C11D 120.8 . . ?
C9D C10D H10D 119.4 . . ?
C11D C10D H10D 119.8 . . ?
C12D C11D C10D 118.8 . . ?
C12D C11D H11D 120.2 . . ?
C10D C11D H11D 121.0 . . ?
C11D C12D C7D 120.6 . . ?
C11D C12D H12D 119.4 . . ?
C7D C12D H12D 120.0 . . ?
C14D C13D C5D 123.7(8) . . ?
C14D C13D C5D 121.9(14) . 5_665 ?
C5D C13D C5D 90.1(12) . 5_665 ?
C14D C13D H13D 106.4 . . ?
C5D C13D H13D 106.4 . . ?
C5D C13D H13D 106.4 5_665 . ?
C19D C14D C15D 118.3 . . ?
C19D C14D C13D 117.9(7) . . ?
C15D C14D C13D 123.3(7) . . ?
C16D C15D C14D 120.5 . . ?
C16D C15D H15D 119.4 . . ?
C14D C15D H15D 120.1 . . ?
C17D C16D C15D 119.5 . . ?
C17D C16D H16D 120.7 . . ?
C15D C16D H16D 119.8 . . ?
C18D C17D C16D 120.4 . . ?
C18D C17D H17D 119.8 . . ?
C16D C17D H17D 119.8 . . ?
C19D C18D C17D 119.8 . . ?
C19D C18D H18D 119.7 . . ?
C17D C18D H18D 120.5 . . ?
C18D C19D C14D 121.5 . . ?
C18D C19D H19D 119.0 . . ?
C14D C19D H19D 119.5 . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_49.9%P_1.0GPa
_database_code_depnum_ccdc_archive 'CCDC 1491728'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_49.9%P_1.0GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.312 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_49.9%P_1.0GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================      
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.88(4)
_cell_length_b                   10.2558(9)
_cell_length_c                   8.4545(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2678(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1000000
_cell_measurement_reflns_used    2282
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      20.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1200000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            15422
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.308
_diffrn_measured_fraction_theta_full 0.312
_diffrn_reflns_Laue_measured_fraction_max 0.308
_diffrn_reflns_Laue_measured_fraction_full 0.312
_diffrn_reflns_point_group_measured_fraction_max 0.308
_diffrn_reflns_point_group_measured_fraction_full 0.312
_reflns_number_total             814
_reflns_number_gt                409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1286P)²+2.2660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         814
_refine_ls_number_parameters     104
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2959
_refine_ls_wR_factor_gt          0.2595
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2M C 0.4150(5) 0.6235(7) 0.2017(9) 0.069(2) Uiso 1 1 d D . . . .
H2M H 0.4121 0.6885 0.2861 0.083 Uiso 1 1 calc R U . A 1
C6M C 0.3729(9) 0.6295(9) 0.1187(11) 0.085(3) Uiso 1 1 d . . . . .
H6M1 H 0.3731 0.5676 0.0319 0.102 Uiso 1 1 calc R U . . .
H6M2 H 0.3692 0.7160 0.0742 0.102 Uiso 1 1 calc R U . . .
C7M C 0.3351(4) 0.5998(6) 0.2256(8) 0.085(3) Uiso 1 1 d G . . . .
C8M C 0.3166(4) 0.4776(5) 0.2238(8) 0.103(3) Uiso 1 1 d G . . . .
H8M H 0.3282 0.4148 0.1552 0.123 Uiso 1 1 d G U . . .
C9M C 0.2823(4) 0.4451(6) 0.3179(10) 0.132(4) Uiso 1 1 d G . . . .
H9M H 0.2708 0.3608 0.3149 0.158 Uiso 1 1 d G U . . .
C10M C 0.2645(4) 0.5363(9) 0.4171(10) 0.157(6) Uiso 1 1 d G . . . .
H10M H 0.2407 0.5144 0.4816 0.188 Uiso 1 1 d G U . . .
C11M C 0.2816(4) 0.6616(7) 0.4224(9) 0.120(4) Uiso 1 1 d G . . . .
H11M H 0.2694 0.7243 0.4894 0.144 Uiso 1 1 d G U . . .
C12M C 0.3172(4) 0.6915(5) 0.3269(9) 0.100(3) Uiso 1 1 d G . . . .
H12M H 0.3292 0.7749 0.3310 0.120 Uiso 1 1 d G U . . .
O1M O 0.4515(15) 0.748(3) -0.003(4) 0.113(14) Uani 0.501(11) 1 d D U P B 1
C1M C 0.4535(7) 0.6714(18) 0.107(2) 0.053(7) Uiso 0.501(11) 1 d D U P B 1
C3M C 0.4328(9) 0.5055(19) 0.286(3) 0.067(9) Uiso 0.501(11) 1 d D U P B 1
H3M1 H 0.4222 0.4267 0.2355 0.081 Uiso 0.501(11) 1 calc R U P B 1
H3M2 H 0.4232 0.5053 0.3951 0.081 Uiso 0.501(11) 1 calc R U P B 1
C4M C 0.4825(9) 0.5088(15) 0.2793(18) 0.040(6) Uiso 0.501(11) 1 d D U P B 1
H4M1 H 0.4943 0.5305 0.3822 0.048 Uiso 0.501(11) 1 calc R U P B 1
H4M2 H 0.4938 0.4246 0.2471 0.048 Uiso 0.501(11) 1 calc R U P B 1
C5M C 0.4938(7) 0.6090(12) 0.1632(14) 0.040(4) Uiso 0.501(11) 1 d D U P B 1
C13M C 0.5326(7) 0.6583(12) 0.1205(16) 0.051(5) Uiso 0.501(11) 1 d D U P B 1
H13M H 0.5313 0.7236 0.0442 0.062 Uiso 0.501(11) 1 calc R U P B 1
C14M C 0.5758(7) 0.6261(12) 0.1739(14) 0.048(4) Uiso 0.501(11) 1 d DG U P B 1
C15M C 0.5832(7) 0.5319(12) 0.2902(14) 0.085(6) Uiso 0.501(11) 1 d DG U P B 1
H15M H 0.5595 0.4863 0.3326 0.102 Uiso 0.501(11) 1 d G U P B 1
C16M C 0.6254(8) 0.5051(11) 0.3438(14) 0.084(6) Uiso 0.501(11) 1 d G U P B 1
H16M H 0.6301 0.4414 0.4212 0.101 Uiso 0.501(11) 1 d G U P B 1
C17M C 0.6603(7) 0.5726(13) 0.2821(16) 0.066(5) Uiso 0.501(11) 1 d G U P B 1
H17M H 0.6887 0.5560 0.3191 0.079 Uiso 0.501(11) 1 d G U P B 1
C18M C 0.6534(7) 0.6644(13) 0.1661(15) 0.076(6) Uiso 0.501(11) 1 d G U P B 1
H18M H 0.6770 0.7102 0.1241 0.092 Uiso 0.501(11) 1 d G U P B 1
C19M C 0.6117(7) 0.6890(10) 0.1117(13) 0.062(6) Uiso 0.501(11) 1 d DG U P B 1
H19M H 0.6075 0.7499 0.0307 0.074 Uiso 0.501(11) 1 d G U P B 1
O1D O 0.4548(14) 0.746(3) 0.012(3) 0.095(13) Uani 0.499(11) 1 d D U P B 2
C1D C 0.4498(7) 0.6459(16) 0.0889(18) 0.043(6) Uiso 0.499(11) 1 d D U P B 2
C3D C 0.4248(9) 0.4869(17) 0.269(3) 0.059(7) Uiso 0.499(11) 1 d D U P B 2
H3D1 H 0.4125 0.4192 0.2025 0.071 Uiso 0.499(11) 1 calc R U P B 2
H3D2 H 0.4138 0.4776 0.3755 0.071 Uiso 0.499(11) 1 calc R U P B 2
C4D C 0.4749(9) 0.4826(17) 0.2658(16) 0.042(5) Uiso 0.499(11) 1 d D U P B 2
H4D1 H 0.4876 0.5372 0.3472 0.051 Uiso 0.499(11) 1 calc R U P B 2
H4D2 H 0.4859 0.3943 0.2756 0.051 Uiso 0.499(11) 1 calc R U P B 2
C5D C 0.4821(5) 0.5380(10) 0.1008(11) 0.043(4) Uiso 0.499(11) 1 d D U P B 2
C13D C 0.5257(5) 0.5733(9) 0.0272(12) 0.040(4) Uiso 0.499(11) 1 d D U P B 2
H13D H 0.5219 0.6570 -0.0269 0.049 Uiso 0.499(11) 1 calc R U P B 2
C14D C 0.5679(5) 0.5814(11) 0.1177(13) 0.049(4) Uiso 0.499(11) 1 d DG U P B 2
C15D C 0.5823(6) 0.4998(10) 0.2391(13) 0.065(4) Uiso 0.499(11) 1 d DG U P B 2
H15D H 0.5638 0.4340 0.2767 0.078 Uiso 0.499(11) 1 d G U P B 2
C16D C 0.6239(6) 0.5151(11) 0.3046(14) 0.058(4) Uiso 0.499(11) 1 d G U P B 2
H16D H 0.6333 0.4596 0.3853 0.070 Uiso 0.499(11) 1 d G U P B 2
C17D C 0.6510(5) 0.6123(14) 0.2498(17) 0.080(6) Uiso 0.499(11) 1 d G U P B 2
H17D H 0.6788 0.6240 0.2948 0.096 Uiso 0.499(11) 1 d G U P B 2
C18D C 0.6374(6) 0.6921(12) 0.1290(17) 0.075(7) Uiso 0.499(11) 1 d G U P B 2
H18D H 0.6558 0.7580 0.0918 0.090 Uiso 0.499(11) 1 d G U P B 2
C19D C 0.5966(6) 0.6752(10) 0.0629(13) 0.070(5) Uiso 0.499(11) 1 d DG U P B 2
H19D H 0.5880 0.7285 -0.0212 0.084 Uiso 0.499(11) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2M C1D 1.455(17) . ?
C2M C6M 1.48(3) . ?
C2M C3M 1.508(16) . ?
C2M C1M 1.516(17) . ?
C2M C3D 1.541(15) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.51(2) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.3776 . ?
C7M C12M 1.3875 . ?
C8M C9M 1.3678 . ?
C8M H8M 0.9366 . ?
C9M C10M 1.3715 . ?
C9M H9M 0.9340 . ?
C10M C11M 1.3900 . ?
C10M H10M 0.9423 . ?
C11M C12M 1.3968 . ?
C11M H11M 0.9367 . ?
C12M H12M 0.9336 . ?
O1M C1M 1.222(16) . ?
C1M C5M 1.478(17) . ?
C3M C4M 1.535(19) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.464(14) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.348(16) . ?
C13M C14M 1.447(15) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.3864 . ?
C14M C15M 1.3979 . ?
C15M C16M 1.4079 . ?
C15M H15M 0.9389 . ?
C16M C17M 1.3829 . ?
C16M H16M 0.9358 . ?
C17M C18M 1.3762 . ?
C17M H17M 0.9461 . ?
C18M C19M 1.3909 . ?
C18M H18M 0.9373 . ?
C19M H19M 0.9356 . ?
O1D C1D 1.222(16) . ?
C1D C5D 1.494(16) . ?
C3D C4D 1.548(19) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.522(14) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.526(15) . ?
C5D C13D 1.592(11) 5_665 ?
C13D C14D 1.514(14) . ?
C13D C5D 1.592(11) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.3864 . ?
C14D C15D 1.3970 . ?
C15D C16D 1.4062 . ?
C15D H15D 0.9388 . ?
C16D C17D 1.3825 . ?
C16D H16D 0.9352 . ?
C17D C18D 1.3753 . ?
C17D H17D 0.9449 . ?
C18D C19D 1.3890 . ?
C18D H18D 0.9371 . ?
C19D H19D 0.9351 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1D C2M C6M 109.4(10) . . ?
C6M C2M C3M 125.3(13) . . ?
C6M C2M C1M 115.1(11) . . ?
C3M C2M C1M 103.0(14) . . ?
C1D C2M C3D 103.9(13) . . ?
C6M C2M C3D 112.6(13) . . ?
C6M C2M H2M 103.7 . . ?
C3M C2M H2M 103.7 . . ?
C1M C2M H2M 103.7 . . ?
C2M C6M C7M 112.8(7) . . ?
C2M C6M H6M1 109.0 . . ?
C7M C6M H6M1 109.0 . . ?
C2M C6M H6M2 109.0 . . ?
C7M C6M H6M2 109.0 . . ?
H6M1 C6M H6M2 107.8 . . ?
C8M C7M C12M 117.3 . . ?
C8M C7M C6M 119.9(6) . . ?
C12M C7M C6M 122.9(6) . . ?
C9M C8M C7M 122.5 . . ?
C9M C8M H8M 119.3 . . ?
C7M C8M H8M 118.3 . . ?
C8M C9M C10M 120.0 . . ?
C8M C9M H9M 120.2 . . ?
C10M C9M H9M 119.8 . . ?
C9M C10M C11M 119.8 . . ?
C9M C10M H10M 120.2 . . ?
C11M C10M H10M 119.9 . . ?
C10M C11M C12M 118.9 . . ?
C10M C11M H11M 120.0 . . ?
C12M C11M H11M 121.1 . . ?
C7M C12M C11M 121.5 . . ?
C7M C12M H12M 119.0 . . ?
C11M C12M H12M 119.5 . . ?
O1M C1M C5M 125(2) . . ?
O1M C1M C2M 125(2) . . ?
C5M C1M C2M 110.4(11) . . ?
C2M C3M C4M 109.2(15) . . ?
C2M C3M H3M1 109.8 . . ?
C4M C3M H3M1 109.8 . . ?
C2M C3M H3M2 109.8 . . ?
C4M C3M H3M2 109.8 . . ?
H3M1 C3M H3M2 108.3 . . ?
C5M C4M C3M 106.2(14) . . ?
C5M C4M H4M1 110.5 . . ?
C3M C4M H4M1 110.5 . . ?
C5M C4M H4M2 110.5 . . ?
C3M C4M H4M2 110.5 . . ?
H4M1 C4M H4M2 108.7 . . ?
C13M C5M C4M 130.9(15) . . ?
C13M C5M C1M 119.9(11) . . ?
C4M C5M C1M 108.6(14) . . ?
C5M C13M C14M 130.5(12) . . ?
C5M C13M H13M 114.8 . . ?
C14M C13M H13M 114.8 . . ?
C19M C14M C15M 117.2 . . ?
C19M C14M C13M 120.9(9) . . ?
C15M C14M C13M 121.9(9) . . ?
C14M C15M C16M 120.9 . . ?
C14M C15M H15M 119.0 . . ?
C16M C15M H15M 120.1 . . ?
C17M C16M C15M 120.2 . . ?
C17M C16M H16M 119.6 . . ?
C15M C16M H16M 120.2 . . ?
C18M C17M C16M 119.4 . . ?
C18M C17M H17M 120.2 . . ?
C16M C17M H17M 120.4 . . ?
C17M C18M C19M 120.2 . . ?
C17M C18M H18M 119.4 . . ?
C19M C18M H18M 120.3 . . ?
C14M C19M C18M 122.1 . . ?
C14M C19M H19M 118.6 . . ?
C18M C19M H19M 119.4 . . ?
O1D C1D C2M 125(2) . . ?
O1D C1D C5D 125(2) . . ?
C2M C1D C5D 109.4(10) . . ?
C2M C3D C4D 102.5(14) . . ?
C2M C3D H3D1 111.3 . . ?
C4D C3D H3D1 111.3 . . ?
C2M C3D H3D2 111.3 . . ?
C4D C3D H3D2 111.3 . . ?
H3D1 C3D H3D2 109.2 . . ?
C5D C4D C3D 98.6(14) . . ?
C5D C4D H4D1 112.1 . . ?
C3D C4D H4D1 112.1 . . ?
C5D C4D H4D2 112.1 . . ?
C3D C4D H4D2 112.1 . . ?
H4D1 C4D H4D2 109.7 . . ?
C1D C5D C4D 103.9(11) . . ?
C1D C5D C13D 112.7(10) . . ?
C4D C5D C13D 126.2(14) . . ?
C1D C5D C13D 112.6(13) . 5_665 ?
C4D C5D C13D 109.5(10) . 5_665 ?
C13D C5D C13D 91.5(9) . 5_665 ?
C14D C13D C5D 124.5(10) . . ?
C14D C13D C5D 120.9(12) . 5_665 ?
C5D C13D C5D 88.5(9) . 5_665 ?
C14D C13D H13D 107.0 . . ?
C5D C13D H13D 107.0 . . ?
C5D C13D H13D 107.0 5_665 . ?
C19D C14D C15D 117.2 . . ?
C19D C14D C13D 114.8(8) . . ?
C15D C14D C13D 127.8(8) . . ?
C14D C15D C16D 120.8 . . ?
C14D C15D H15D 119.1 . . ?
C16D C15D H15D 120.1 . . ?
C17D C16D C15D 120.2 . . ?
C17D C16D H16D 119.7 . . ?
C15D C16D H16D 120.2 . . ?
C18D C17D C16D 119.5 . . ?
C18D C17D H17D 120.1 . . ?
C16D C17D H17D 120.4 . . ?
C17D C18D C19D 120.2 . . ?
C17D C18D H18D 119.5 . . ?
C19D C18D H18D 120.3 . . ?
C14D C19D C18D 122.1 . . ?
C14D C19D H19D 118.6 . . ?
C18D C19D H19D 119.3 . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.031

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_100%P_1.0GPa
_database_code_depnum_ccdc_archive 'CCDC 1491729'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_100%P_1.0GPa        
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.367 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
# end Validation Reply Form
#====================================================================       
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.68(3)
_cell_length_b                   10.3153(7)
_cell_length_c                   8.3651(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2647(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1000000
_cell_measurement_reflns_used    3041
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1200000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            15256
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.205
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.315
_diffrn_measured_fraction_theta_full 0.317
_diffrn_reflns_Laue_measured_fraction_max 0.315
_diffrn_reflns_Laue_measured_fraction_full 0.317
_diffrn_reflns_point_group_measured_fraction_max 0.315
_diffrn_reflns_point_group_measured_fraction_full 0.317
_reflns_number_total             821
_reflns_number_gt                520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²+3.1264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         821
_refine_ls_number_parameters     112
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1734
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1D O 0.4518(4) 0.7428(3) 0.0232(5) 0.076(7) Uani 1 1 d . . . . .
C1D C 0.4504(5) 0.6457(4) 0.1047(6) 0.0361(14) Uiso 1 1 d . . . . .
C2D C 0.4136(6) 0.6201(5) 0.2258(7) 0.0487(17) Uiso 1 1 d . . . . .
H2D H 0.4146 0.6890 0.3064 0.058 Uiso 1 1 calc R U . . .
C3D C 0.4287(8) 0.4947(5) 0.3052(8) 0.045(2) Uiso 1 1 d . . . . .
H3D1 H 0.4150 0.4202 0.2556 0.054 Uiso 1 1 calc R U . . .
H3D2 H 0.4216 0.4950 0.4182 0.054 Uiso 1 1 calc R U . . .
C4D C 0.4781(7) 0.4908(5) 0.2810(7) 0.0384(18) Uiso 1 1 d . . . . .
H4D1 H 0.4894 0.4036 0.2937 0.046 Uiso 1 1 calc R U . . .
H4D2 H 0.4930 0.5483 0.3547 0.046 Uiso 1 1 calc R U . . .
C5D C 0.4826(5) 0.5381(4) 0.1067(5) 0.0314(13) Uiso 1 1 d . . . . .
C6D C 0.3702(6) 0.6255(6) 0.1466(8) 0.060(2) Uiso 1 1 d . . . . .
H6D1 H 0.3699 0.5651 0.0578 0.072 Uiso 1 1 calc R U . . .
H6D2 H 0.3658 0.7119 0.1035 0.072 Uiso 1 1 calc R U . . .
C7D C 0.3326(4) 0.5935(5) 0.2578(6) 0.0604(19) Uiso 1 1 d G . . . .
C8D C 0.3154(4) 0.4698(4) 0.2555(7) 0.091(14) Uani 1 1 d G . . . .
H8D H 0.3272 0.4089 0.1848 0.109 Uiso 1 1 d G U . . .
C9D C 0.2819(4) 0.4332(5) 0.3523(8) 0.083(17) Uani 1 1 d G . . . .
H9D H 0.2713 0.3480 0.3489 0.100 Uiso 1 1 d G U . . .
C10D C 0.2637(3) 0.5216(8) 0.4548(8) 0.107(19) Uani 1 1 d G . . . .
H10D H 0.2406 0.4968 0.5213 0.128 Uiso 1 1 d G U . . .
C11D C 0.2796(4) 0.6482(7) 0.4607(7) 0.096(16) Uani 1 1 d G . . . .
H11D H 0.2671 0.7089 0.5300 0.115 Uiso 1 1 d G U . . .
C12D C 0.3143(4) 0.6823(4) 0.3624(7) 0.106(15) Uani 1 1 d G . . . .
H12D H 0.3255 0.7667 0.3669 0.128 Uiso 1 1 d G U . . .
C13D C 0.5260(5) 0.5738(4) 0.0215(6) 0.0337(15) Uiso 1 1 d . . . . .
H13D H 0.5212 0.6565 -0.0332 0.040 Uiso 1 1 calc R U . . .
C14D C 0.5683(3) 0.5841(4) 0.1054(5) 0.0348(14) Uiso 1 1 d G . . . .
C15D C 0.5829(3) 0.4983(3) 0.2227(5) 0.071(8) Uani 1 1 d G U . . .
H15D H 0.5641 0.4333 0.2602 0.086 Uiso 1 1 d G U . . .
C16D C 0.6251(3) 0.5083(5) 0.2844(5) 0.079(8) Uani 1 1 d G U . . .
H16D H 0.6347 0.4499 0.3624 0.095 Uiso 1 1 d G U . . .
C17D C 0.6527(3) 0.6043(6) 0.2299(6) 0.094(8) Uani 1 1 d G U . . .
H17D H 0.6809 0.6124 0.2725 0.113 Uiso 1 1 d G U . . .
C18D C 0.6388(3) 0.6883(4) 0.1131(6) 0.087(8) Uani 1 1 d G U . . .
H18D H 0.6575 0.7533 0.0760 0.104 Uiso 1 1 d G U . . .
C19D C 0.5973(3) 0.6766(3) 0.0507(5) 0.079(8) Uani 1 1 d G U . . .
H19D H 0.5886 0.7327 -0.0309 0.095 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1D C1D 1.212(6) . ?
C1D C5D 1.486(15) . ?
C1D C2D 1.54(2) . ?
C2D C6D 1.49(2) . ?
C2D C3D 1.526(12) . ?
C2D H2D 0.9800 . ?
C3D C4D 1.53(3) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.543(8) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.555(18) . ?
C5D C13D 1.598(7) 5_665 ?
C6D C7D 1.518(18) . ?
C6D H6D1 0.9700 . ?
C6D H6D2 0.9700 . ?
C7D C8D 1.3815 . ?
C7D C12D 1.3862 . ?
C8D C9D 1.3614 . ?
C8D H8D 0.9358 . ?
C9D C10D 1.3703 . ?
C9D H9D 0.9370 . ?
C10D C11D 1.3944 . ?
C10D H10D 0.9378 . ?
C11D C12D 1.3901 . ?
C11D H11D 0.9358 . ?
C12D H12D 0.9363 . ?
C13D C14D 1.477(16) . ?
C13D C5D 1.598(7) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.3843 . ?
C14D C15D 1.3958 . ?
C15D C16D 1.3982 . ?
C15D H15D 0.9378 . ?
C16D C17D 1.3811 . ?
C16D H16D 0.9345 . ?
C17D C18D 1.3740 . ?
C17D H17D 0.9396 . ?
C18D C19D 1.3811 . ?
C18D H18D 0.9361 . ?
C19D H19D 0.9342 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1D C1D C5D 126.9(11) . . ?
O1D C1D C2D 122.5(11) . . ?
C5D C1D C2D 110.6(6) . . ?
C6D C2D C3D 119.9(12) . . ?
C6D C2D C1D 110.9(6) . . ?
C3D C2D C1D 102.1(13) . . ?
C6D C2D H2D 107.8 . . ?
C3D C2D H2D 107.8 . . ?
C1D C2D H2D 107.8 . . ?
C2D C3D C4D 105.4(11) . . ?
C2D C3D H3D1 110.7 . . ?
C4D C3D H3D1 110.7 . . ?
C2D C3D H3D2 110.7 . . ?
C4D C3D H3D2 110.7 . . ?
H3D1 C3D H3D2 108.8 . . ?
C3D C4D C5D 101.8(11) . . ?
C3D C4D H4D1 111.4 . . ?
C5D C4D H4D1 111.4 . . ?
C3D C4D H4D2 111.4 . . ?
C5D C4D H4D2 111.4 . . ?
H4D1 C4D H4D2 109.3 . . ?
C1D C5D C4D 100.8(8) . . ?
C1D C5D C13D 112.8(6) . . ?
C4D C5D C13D 125.7(12) . . ?
C1D C5D C13D 114.9(9) . 5_665 ?
C4D C5D C13D 113.0(5) . 5_665 ?
C13D C5D C13D 90.3(7) . 5_665 ?
C2D C6D C7D 113.5(7) . . ?
C2D C6D H6D1 108.9 . . ?
C7D C6D H6D1 108.9 . . ?
C2D C6D H6D2 108.9 . . ?
C7D C6D H6D2 108.9 . . ?
H6D1 C6D H6D2 107.7 . . ?
C8D C7D C12D 117.7 . . ?
C8D C7D C6D 118.9(5) . . ?
C12D C7D C6D 123.4(5) . . ?
C9D C8D C7D 122.4 . . ?
C9D C8D H8D 118.9 . . ?
C7D C8D H8D 118.7 . . ?
C8D C9D C10D 119.6 . . ?
C8D C9D H9D 120.2 . . ?
C10D C9D H9D 120.1 . . ?
C9D C10D C11D 120.2 . . ?
C9D C10D H10D 119.8 . . ?
C11D C10D H10D 119.9 . . ?
C12D C11D C10D 118.9 . . ?
C12D C11D H11D 120.7 . . ?
C10D C11D H11D 120.4 . . ?
C7D C12D C11D 121.1 . . ?
C7D C12D H12D 119.4 . . ?
C11D C12D H12D 119.5 . . ?
C14D C13D C5D 123.4(5) . . ?
C14D C13D C5D 121.1(9) . 5_665 ?
C5D C13D C5D 89.7(7) . 5_665 ?
C14D C13D H13D 106.9 . . ?
C5D C13D H13D 106.9 . . ?
C5D C13D H13D 106.9 5_665 . ?
C19D C14D C15D 117.6 . . ?
C19D C14D C13D 117.2(4) . . ?
C15D C14D C13D 124.8(4) . . ?
C14D C15D C16D 120.7 . . ?
C14D C15D H15D 119.4 . . ?
C16D C15D H15D 119.9 . . ?
C17D C16D C15D 120.0 . . ?
C17D C16D H16D 120.0 . . ?
C15D C16D H16D 120.0 . . ?
C18D C17D C16D 119.8 . . ?
C18D C17D H17D 120.0 . . ?
C16D C17D H17D 120.3 . . ?
C17D C18D C19D 120.0 . . ?
C17D C18D H18D 119.8 . . ?
C19D C18D H18D 120.2 . . ?
C18D C19D C14D 121.9 . . ?
C18D C19D H19D 119.2 . . ?
C14D C19D H19D 118.9 . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_80.4%P_1.2GPa
_database_code_depnum_ccdc_archive 'CCDC 1491730'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_80.4%P_1.2GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.343 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_80.4%P_1.2GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================     
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.37(3)
_cell_length_b                   10.2318(12)
_cell_length_c                   8.3984(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2610(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1200000
_cell_measurement_reflns_used    1852
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      25.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1200000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            15508
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.1439
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.340
_diffrn_measured_fraction_theta_full 0.343
_diffrn_reflns_Laue_measured_fraction_max 0.340
_diffrn_reflns_Laue_measured_fraction_full 0.343
_diffrn_reflns_point_group_measured_fraction_max 0.340
_diffrn_reflns_point_group_measured_fraction_full 0.343
_reflns_number_total             877
_reflns_number_gt                404
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1122P)²+6.6661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         877
_refine_ls_number_parameters     99
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.1957
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.2998
_refine_ls_wR_factor_gt          0.2315
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2M C 0.4139(6) 0.6224(8) 0.2199(12) 0.064(3) Uiso 1 1 d D . . . .
H2M H 0.4114 0.6915 0.3002 0.077 Uiso 1 1 calc R U . A 1
C6M C 0.3702(9) 0.6285(10) 0.1392(13) 0.080(4) Uiso 1 1 d . . . . .
H6M1 H 0.3701 0.5679 0.0503 0.096 Uiso 1 1 calc R U . . .
H6M2 H 0.3658 0.7158 0.0969 0.096 Uiso 1 1 calc R U . . .
C7M C 0.3325(4) 0.5955(7) 0.2501(9) 0.073(3) Uiso 1 1 d G . . . .
C8M C 0.3155(5) 0.4714(6) 0.2481(9) 0.081(3) Uiso 1 1 d G . . . .
H8M H 0.3273 0.4106 0.1775 0.097 Uiso 1 1 d G U . . .
C9M C 0.2823(5) 0.4342(6) 0.3452(11) 0.102(5) Uiso 1 1 d G . . . .
H9M H 0.2718 0.3487 0.3420 0.123 Uiso 1 1 d G U . . .
C10M C 0.2642(4) 0.5224(9) 0.4476(11) 0.121(5) Uiso 1 1 d G . . . .
H10M H 0.2412 0.4972 0.5142 0.145 Uiso 1 1 d G U . . .
C11M C 0.2798(5) 0.6494(7) 0.4532(10) 0.104(5) Uiso 1 1 d G . . . .
H11M H 0.2674 0.7100 0.5224 0.124 Uiso 1 1 d G U . . .
C12M C 0.3143(5) 0.6841(5) 0.3546(9) 0.082(4) Uiso 1 1 d G . . . .
H12M H 0.3253 0.7688 0.3588 0.098 Uiso 1 1 d G U . . .
O1M O 0.448(2) 0.769(4) 0.031(6) 0.030(12) Uiso 0.196(13) 1 d D U P B 1
C1M C 0.4505(10) 0.673(4) 0.114(5) 0.034(13) Uiso 0.196(13) 1 d D U P B 1
C3M C 0.4330(13) 0.513(4) 0.313(6) 0.039(14) Uiso 0.196(13) 1 d D U P B 1
H3M1 H 0.4215 0.4300 0.2743 0.047 Uiso 0.196(13) 1 calc R U P B 1
H3M2 H 0.4253 0.5214 0.4244 0.047 Uiso 0.196(13) 1 calc R U P B 1
C4M C 0.4827(12) 0.517(4) 0.293(5) 0.039(9) Uiso 0.196(13) 1 d D U P B 1
H4M1 H 0.4965 0.5511 0.3884 0.047 Uiso 0.196(13) 1 calc R U P B 1
H4M2 H 0.4941 0.4297 0.2732 0.047 Uiso 0.196(13) 1 calc R U P B 1
C5M C 0.4914(10) 0.603(4) 0.155(4) 0.045(12) Uiso 0.196(13) 1 d D U P B 1
C13M C 0.5302(11) 0.650(4) 0.107(6) 0.066(14) Uiso 0.196(13) 1 d D U P B 1
H13M H 0.5269 0.7111 0.0262 0.079 Uiso 0.196(13) 1 calc R U P B 1
C14M C 0.5756(11) 0.630(3) 0.148(4) 0.047(9) Uiso 0.196(13) 1 d DG U P B 1
C15M C 0.5926(14) 0.545(3) 0.260(4) 0.052(13) Uiso 0.196(13) 1 d DG U P B 1
H15M H 0.5736 0.4897 0.3157 0.062 Uiso 0.196(13) 1 d G U P B 1
C16M C 0.6374(15) 0.540(4) 0.290(4) 0.046(6) Uiso 0.196(13) 1 d G U P B 1
H16M H 0.6484 0.4816 0.3653 0.056 Uiso 0.196(13) 1 d G U P B 1
C17M C 0.6653(12) 0.621(4) 0.209(5) 0.072(9) Uiso 0.196(13) 1 d G U P B 1
H17M H 0.6954 0.6195 0.2303 0.087 Uiso 0.196(13) 1 d G U P B 1
C18M C 0.6490(13) 0.705(4) 0.097(5) 0.081(15) Uiso 0.196(13) 1 d G U P B 1
H18M H 0.6680 0.7600 0.0414 0.098 Uiso 0.196(13) 1 d G U P B 1
C19M C 0.6048(13) 0.708(3) 0.065(4) 0.041(8) Uiso 0.196(13) 1 d DG U P B 1
H19M H 0.5942 0.7632 -0.0134 0.049 Uiso 0.196(13) 1 d G U P B 1
O1D O 0.4525(7) 0.7401(12) 0.0161(17) 0.072(9) Uani 0.804(13) 1 d D U P B 2
C1D C 0.4493(6) 0.6452(12) 0.1016(15) 0.047(5) Uiso 0.804(13) 1 d D U P B 2
C3D C 0.4275(8) 0.4914(13) 0.2956(19) 0.058(6) Uiso 0.804(13) 1 d D U P B 2
H3D1 H 0.4193 0.4884 0.4071 0.070 Uiso 0.804(13) 1 calc R U P B 2
H3D2 H 0.4137 0.4186 0.2407 0.070 Uiso 0.804(13) 1 calc R U P B 2
C4D C 0.4777(7) 0.4869(12) 0.2763(13) 0.045(4) Uiso 0.804(13) 1 d D U P B 2
H4D1 H 0.4923 0.5439 0.3520 0.054 Uiso 0.804(13) 1 calc R U P B 2
H4D2 H 0.4890 0.3987 0.2880 0.054 Uiso 0.804(13) 1 calc R U P B 2
C5D C 0.4828(5) 0.5367(8) 0.1051(9) 0.038(3) Uiso 0.804(13) 1 d D U P B 2
C13D C 0.5261(4) 0.5744(8) 0.0229(10) 0.038(3) Uiso 0.804(13) 1 d D U P B 2
H13D H 0.5213 0.6587 -0.0299 0.046 Uiso 0.804(13) 1 calc R U P B 2
C14D C 0.5693(4) 0.5831(9) 0.1105(10) 0.045(3) Uiso 0.804(13) 1 d DG U P B 2
C15D C 0.5824(4) 0.4971(8) 0.2293(10) 0.053(4) Uiso 0.804(13) 1 d DG U P B 2
H15D H 0.5628 0.4338 0.2658 0.063 Uiso 0.804(13) 1 d G U P B 2
C16D C 0.6243(4) 0.5043(9) 0.2938(11) 0.052(4) Uiso 0.804(13) 1 d G U P B 2
H16D H 0.6329 0.4458 0.3727 0.062 Uiso 0.804(13) 1 d G U P B 2
C17D C 0.6531(4) 0.5978(11) 0.2407(15) 0.085(5) Uiso 0.804(13) 1 d G U P B 2
H17D H 0.6811 0.6041 0.2850 0.102 Uiso 0.804(13) 1 d G U P B 2
C18D C 0.6407(4) 0.6820(9) 0.1224(13) 0.065(4) Uiso 0.804(13) 1 d G U P B 2
H18D H 0.6602 0.7453 0.0863 0.078 Uiso 0.804(13) 1 d G U P B 2
C19D C 0.5995(4) 0.6730(8) 0.0573(9) 0.053(4) Uiso 0.804(13) 1 d DG U P B 2
H19D H 0.5917 0.7291 -0.0251 0.064 Uiso 0.804(13) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2M C1D 1.482(16) . ?
C2M C3M 1.485(19) . ?
C2M C6M 1.49(3) . ?
C2M C1M 1.512(19) . ?
C2M C3D 1.540(13) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.51(2) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.3715 . ?
C7M C12M 1.3785 . ?
C8M C9M 1.3515 . ?
C8M H8M 0.9307 . ?
C9M C10M 1.3627 . ?
C9M H9M 0.9302 . ?
C10M C11M 1.3844 . ?
C10M H10M 0.9311 . ?
C11M C12M 1.3800 . ?
C11M H11M 0.9307 . ?
C12M H12M 0.9296 . ?
O1M C1M 1.212(18) . ?
C1M C5M 1.472(18) . ?
C3M C4M 1.52(2) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.482(19) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.333(18) . ?
C13M C14M 1.435(17) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.3736 . ?
C14M C15M 1.3890 . ?
C15M C16M 1.3851 . ?
C15M H15M 0.9306 . ?
C16M C17M 1.3707 . ?
C16M H16M 0.9299 . ?
C17M C18M 1.3674 . ?
C17M H17M 0.9308 . ?
C18M C19M 1.3682 . ?
C18M H18M 0.9291 . ?
C19M H19M 0.9298 . ?
O1D C1D 1.212(11) . ?
C1D C5D 1.507(14) . ?
C3D C4D 1.533(18) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.533(12) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.533(14) . ?
C5D C13D 1.589(10) 5_665 ?
C13D C14D 1.507(13) . ?
C13D C5D 1.589(10) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.3736 . ?
C14D C15D 1.3890 . ?
C15D C16D 1.3850 . ?
C15D H15D 0.9308 . ?
C16D C17D 1.3707 . ?
C16D H16D 0.9299 . ?
C17D C18D 1.3674 . ?
C17D H17D 0.9308 . ?
C18D C19D 1.3682 . ?
C18D H18D 0.9291 . ?
C19D H19D 0.9298 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1D C2M C6M 109.5(11) . . ?
C3M C2M C6M 128(2) . . ?
C3M C2M C1M 106.2(17) . . ?
C6M C2M C1M 111.9(19) . . ?
C1D C2M C3D 102.6(11) . . ?
C6M C2M C3D 117.6(12) . . ?
C3M C2M H2M 102.4 . . ?
C6M C2M H2M 102.4 . . ?
C1M C2M H2M 102.4 . . ?
C2M C6M C7M 112.6(9) . . ?
C2M C6M H6M1 109.1 . . ?
C7M C6M H6M1 109.1 . . ?
C2M C6M H6M2 109.1 . . ?
C7M C6M H6M2 109.1 . . ?
H6M1 C6M H6M2 107.8 . . ?
C8M C7M C12M 117.7 . . ?
C8M C7M C6M 119.0(7) . . ?
C12M C7M C6M 123.3(7) . . ?
C9M C8M C7M 122.3 . . ?
C9M C8M H8M 118.9 . . ?
C7M C8M H8M 118.7 . . ?
C8M C9M C10M 119.7 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.2 . . ?
C9M C10M C11M 120.3 . . ?
C9M C10M H10M 119.9 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.7 . . ?
C10M C11M H11M 120.4 . . ?
C7M C12M C11M 121.1 . . ?
C7M C12M H12M 119.5 . . ?
C11M C12M H12M 119.4 . . ?
O1M C1M C5M 125(3) . . ?
O1M C1M C2M 125(3) . . ?
C5M C1M C2M 108.6(16) . . ?
C2M C3M C4M 108.1(19) . . ?
C2M C3M H3M1 110.1 . . ?
C4M C3M H3M1 110.1 . . ?
C2M C3M H3M2 110.1 . . ?
C4M C3M H3M2 110.1 . . ?
H3M1 C3M H3M2 108.4 . . ?
C5M C4M C3M 106.2(18) . . ?
C5M C4M H4M1 110.5 . . ?
C3M C4M H4M1 110.5 . . ?
C5M C4M H4M2 110.5 . . ?
C3M C4M H4M2 110.5 . . ?
H4M1 C4M H4M2 108.7 . . ?
C13M C5M C1M 120(2) . . ?
C13M C5M C4M 127(2) . . ?
C1M C5M C4M 108.7(17) . . ?
C5M C13M C14M 137(3) . . ?
C5M C13M H13M 111.6 . . ?
C14M C13M H13M 111.6 . . ?
C19M C14M C15M 117.8 . . ?
C19M C14M C13M 115.0(19) . . ?
C15M C14M C13M 127.2(19) . . ?
C16M C15M C14M 120.7 . . ?
C16M C15M H15M 119.7 . . ?
C14M C15M H15M 119.6 . . ?
C17M C16M C15M 119.7 . . ?
C17M C16M H16M 120.2 . . ?
C15M C16M H16M 120.1 . . ?
C18M C17M C16M 120.0 . . ?
C18M C17M H17M 120.0 . . ?
C16M C17M H17M 120.0 . . ?
C17M C18M C19M 120.1 . . ?
C17M C18M H18M 120.0 . . ?
C19M C18M H18M 119.9 . . ?
C18M C19M C14M 121.7 . . ?
C18M C19M H19M 119.2 . . ?
C14M C19M H19M 119.1 . . ?
O1D C1D C2M 125.6(13) . . ?
O1D C1D C5D 123.2(14) . . ?
C2M C1D C5D 111.2(8) . . ?
C4D C3D C2M 104.4(12) . . ?
C4D C3D H3D1 110.9 . . ?
C2M C3D H3D1 110.9 . . ?
C4D C3D H3D2 110.9 . . ?
C2M C3D H3D2 110.9 . . ?
H3D1 C3D H3D2 108.9 . . ?
C5D C4D C3D 100.9(12) . . ?
C5D C4D H4D1 111.6 . . ?
C3D C4D H4D1 111.6 . . ?
C5D C4D H4D2 111.6 . . ?
C3D C4D H4D2 111.6 . . ?
H4D1 C4D H4D2 109.4 . . ?
C1D C5D C13D 112.6(8) . . ?
C1D C5D C4D 101.2(9) . . ?
C13D C5D C4D 126.4(12) . . ?
C1D C5D C13D 113.5(11) . 5_665 ?
C13D C5D C13D 91.2(8) . 5_665 ?
C4D C5D C13D 112.3(8) . 5_665 ?
C14D C13D C5D 122.7(8) . . ?
C14D C13D C5D 121.4(10) . 5_665 ?
C5D C13D C5D 88.8(8) . 5_665 ?
C14D C13D H13D 107.3 . . ?
C5D C13D H13D 107.3 . . ?
C5D C13D H13D 107.3 5_665 . ?
C19D C14D C15D 117.8 . . ?
C19D C14D C13D 117.5(6) . . ?
C15D C14D C13D 124.3(6) . . ?
C16D C15D C14D 120.7 . . ?
C16D C15D H15D 119.7 . . ?
C14D C15D H15D 119.6 . . ?
C17D C16D C15D 119.7 . . ?
C17D C16D H16D 120.2 . . ?
C15D C16D H16D 120.1 . . ?
C18D C17D C16D 120.0 . . ?
C18D C17D H17D 120.0 . . ?
C16D C17D H17D 120.0 . . ?
C17D C18D C19D 120.1 . . ?
C17D C18D H18D 120.0 . . ?
C19D C18D H18D 119.9 . . ?
C18D C19D C14D 121.7 . . ?
C18D C19D H19D 119.2 . . ?
C14D C19D H19D 119.1 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_100%P_1.2GPa
_database_code_depnum_ccdc_archive 'CCDC 1491731'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_100%P_1.2GPa        
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.342 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_100%P_1.2GPa        
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================    
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.46(3)
_cell_length_b                   10.2338(10)
_cell_length_c                   8.3341(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2598(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1200000
_cell_measurement_reflns_used    1995
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      20.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1200000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            15316
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.1335
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.223
_diffrn_reflns_theta_max         25.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.339
_diffrn_measured_fraction_theta_full 0.342
_diffrn_reflns_Laue_measured_fraction_max 0.339
_diffrn_reflns_Laue_measured_fraction_full 0.342
_diffrn_reflns_point_group_measured_fraction_max 0.339
_diffrn_reflns_point_group_measured_fraction_full 0.342
_reflns_number_total             866
_reflns_number_gt                436
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1522P)²+5.8933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         866
_refine_ls_number_parameters     62
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1820
_refine_ls_R_factor_gt           0.1028
_refine_ls_wR_factor_ref         0.3321
_refine_ls_wR_factor_gt          0.2758
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1D O 0.4522(5) 0.7453(5) 0.0250(7) 0.079(9) Uani 1 1 d . . . . .
C1D C 0.4505(8) 0.6456(7) 0.1070(10) 0.043(2) Uiso 1 1 d . . . . .
C2D C 0.4151(8) 0.6211(8) 0.2276(12) 0.055(3) Uiso 1 1 d . . . . .
H2D H 0.4165 0.6906 0.3084 0.066 Uiso 1 1 calc R U . . .
C3D C 0.4281(10) 0.4936(8) 0.3079(12) 0.052(3) Uiso 1 1 d . . . . .
H3D1 H 0.4143 0.4194 0.2563 0.062 Uiso 1 1 calc R U . . .
H3D2 H 0.4205 0.4938 0.4209 0.062 Uiso 1 1 calc R U . . .
C4D C 0.4791(9) 0.4916(8) 0.2834(11) 0.045(3) Uiso 1 1 d . . . . .
H4D1 H 0.4938 0.5517 0.3557 0.055 Uiso 1 1 calc R U . . .
H4D2 H 0.4910 0.4045 0.2980 0.055 Uiso 1 1 calc R U . . .
C5D C 0.4827(7) 0.5367(7) 0.1078(9) 0.037(2) Uiso 1 1 d . . . . .
C6D C 0.3693(10) 0.6273(10) 0.1467(13) 0.071(3) Uiso 1 1 d . . . . .
H6D1 H 0.3647 0.7147 0.1049 0.086 Uiso 1 1 calc R U . . .
H6D2 H 0.3688 0.5672 0.0567 0.086 Uiso 1 1 calc R U . . .
C7D C 0.3322(4) 0.5936(7) 0.2596(8) 0.063(3) Uiso 1 1 d G . . . .
C8D C 0.3156(5) 0.4691(6) 0.2578(9) 0.069(3) Uiso 1 1 d G . . . .
H8D H 0.3277 0.4088 0.1869 0.082 Uiso 1 1 d G U . . .
C9D C 0.2824(5) 0.4312(6) 0.3551(11) 0.086(4) Uiso 1 1 d G . . . .
H9D H 0.2723 0.3456 0.3520 0.103 Uiso 1 1 d G U . . .
C10D C 0.2639(4) 0.5189(8) 0.4578(11) 0.105(5) Uiso 1 1 d G . . . .
H10D H 0.2410 0.4931 0.5246 0.125 Uiso 1 1 d G U . . .
C11D C 0.2792(5) 0.6461(7) 0.4633(10) 0.084(4) Uiso 1 1 d G . . . .
H11D H 0.2665 0.7064 0.5327 0.101 Uiso 1 1 d G U . . .
C12D C 0.3136(5) 0.6817(5) 0.3645(9) 0.074(3) Uiso 1 1 d G . . . .
H12D H 0.3244 0.7666 0.3686 0.089 Uiso 1 1 d G U . . .
C13D C 0.5249(7) 0.5745(7) 0.0218(10) 0.041(2) Uiso 1 1 d . . . . .
H13D H 0.5195 0.6583 -0.0315 0.049 Uiso 1 1 calc R U . . .
C14D C 0.5690(4) 0.5854(6) 0.1062(8) 0.046(2) Uiso 1 1 d G . . . .
C15D C 0.5841(4) 0.5005(5) 0.2237(7) 0.053(3) Uiso 1 1 d G . . . .
H15D H 0.5654 0.4359 0.2631 0.063 Uiso 1 1 d G U . . .
C16D C 0.6266(4) 0.5107(5) 0.2828(7) 0.061(3) Uiso 1 1 d G . . . .
H16D H 0.6364 0.4530 0.3610 0.073 Uiso 1 1 d G U . . .
C17D C 0.6540(4) 0.6061(7) 0.2255(9) 0.078(4) Uiso 1 1 d G . . . .
H17D H 0.6824 0.6144 0.2663 0.094 Uiso 1 1 d G U . . .
C18D C 0.6397(4) 0.6892(5) 0.1084(8) 0.068(3) Uiso 1 1 d G . . . .
H18D H 0.6583 0.7538 0.0694 0.082 Uiso 1 1 d G U . . .
C19D C 0.5979(4) 0.6773(5) 0.0485(7) 0.057(3) Uiso 1 1 d G . . . .
H19D H 0.5888 0.7327 -0.0332 0.069 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1D C1D 1.228(9) . ?
C1D C5D 1.48(2) . ?
C1D C2D 1.50(3) . ?
C2D C3D 1.519(15) . ?
C2D C6D 1.55(4) . ?
C2D H2D 0.9800 . ?
C3D C4D 1.57(3) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.539(12) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.52(3) . ?
C5D C13D 1.586(11) 5_665 ?
C6D C7D 1.51(3) . ?
C6D H6D1 0.9700 . ?
C6D H6D2 0.9700 . ?
C7D C8D 1.3708 . ?
C7D C12D 1.3778 . ?
C8D C9D 1.3531 . ?
C8D H8D 0.9301 . ?
C9D C10D 1.3620 . ?
C9D H9D 0.9296 . ?
C10D C11D 1.3834 . ?
C10D H10D 0.9321 . ?
C11D C12D 1.3817 . ?
C11D H11D 0.9301 . ?
C12D H12D 0.9290 . ?
C13D C14D 1.52(2) . ?
C13D C5D 1.586(11) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.3744 . ?
C14D C15D 1.3878 . ?
C15D C16D 1.3888 . ?
C15D H15D 0.9311 . ?
C16D C17D 1.3713 . ?
C16D H16D 0.9291 . ?
C17D C18D 1.3662 . ?
C17D H17D 0.9333 . ?
C18D C19D 1.3718 . ?
C18D H18D 0.9295 . ?
C19D H19D 0.9290 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1D C1D C5D 126.8(16) . . ?
O1D C1D C2D 122.9(15) . . ?
C5D C1D C2D 110.3(9) . . ?
C1D C2D C3D 104.6(18) . . ?
C1D C2D C6D 110.5(10) . . ?
C3D C2D C6D 117.5(16) . . ?
C1D C2D H2D 108.0 . . ?
C3D C2D H2D 108.0 . . ?
C6D C2D H2D 108.0 . . ?
C2D C3D C4D 102.2(16) . . ?
C2D C3D H3D1 111.3 . . ?
C4D C3D H3D1 111.3 . . ?
C2D C3D H3D2 111.3 . . ?
C4D C3D H3D2 111.3 . . ?
H3D1 C3D H3D2 109.2 . . ?
C5D C4D C3D 101.0(16) . . ?
C5D C4D H4D1 111.6 . . ?
C3D C4D H4D1 111.6 . . ?
C5D C4D H4D2 111.6 . . ?
C3D C4D H4D2 111.6 . . ?
H4D1 C4D H4D2 109.4 . . ?
C1D C5D C13D 111.3(9) . . ?
C1D C5D C4D 100.5(11) . . ?
C13D C5D C4D 125.8(17) . . ?
C1D C5D C13D 116.1(13) . 5_665 ?
C13D C5D C13D 89.1(10) . 5_665 ?
C4D C5D C13D 115.0(8) . 5_665 ?
C7D C6D C2D 113.1(10) . . ?
C7D C6D H6D1 109.0 . . ?
C2D C6D H6D1 109.0 . . ?
C7D C6D H6D2 109.0 . . ?
C2D C6D H6D2 109.0 . . ?
H6D1 C6D H6D2 107.8 . . ?
C8D C7D C12D 117.6 . . ?
C8D C7D C6D 118.8(6) . . ?
C12D C7D C6D 123.6(6) . . ?
C9D C8D C7D 122.4 . . ?
C9D C8D H8D 119.0 . . ?
C7D C8D H8D 118.6 . . ?
C8D C9D C10D 119.8 . . ?
C8D C9D H9D 120.2 . . ?
C10D C9D H9D 120.1 . . ?
C9D C10D C11D 120.2 . . ?
C9D C10D H10D 120.0 . . ?
C11D C10D H10D 119.9 . . ?
C12D C11D C10D 118.9 . . ?
C12D C11D H11D 120.8 . . ?
C10D C11D H11D 120.3 . . ?
C7D C12D C11D 121.2 . . ?
C7D C12D H12D 119.3 . . ?
C11D C12D H12D 119.5 . . ?
C14D C13D C5D 123.2(8) . . ?
C14D C13D C5D 119.7(12) . 5_665 ?
C5D C13D C5D 90.9(10) . 5_665 ?
C14D C13D H13D 107.1 . . ?
C5D C13D H13D 107.1 . . ?
C5D C13D H13D 107.1 5_665 . ?
C19D C14D C15D 117.6 . . ?
C19D C14D C13D 117.0(6) . . ?
C15D C14D C13D 124.9(6) . . ?
C14D C15D C16D 120.8 . . ?
C14D C15D H15D 119.4 . . ?
C16D C15D H15D 119.8 . . ?
C17D C16D C15D 119.9 . . ?
C17D C16D H16D 120.0 . . ?
C15D C16D H16D 120.1 . . ?
C18D C17D C16D 119.8 . . ?
C18D C17D H17D 120.0 . . ?
C16D C17D H17D 120.2 . . ?
C17D C18D C19D 120.1 . . ?
C17D C18D H18D 119.8 . . ?
C19D C18D H18D 120.1 . . ?
C18D C19D C14D 121.8 . . ?
C18D C19D H19D 119.2 . . ?
C14D C19D H19D 118.9 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.051

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12.1%P_0.7GPa
_database_code_depnum_ccdc_archive 'CCDC 1496289'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#====================================================================
# start Validation Reply Form
_vrf_PLAT029_12.1%P_0.7GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.396 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_12.1%P_0.7GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#==================================================================== 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.934(2)
_cell_length_b                   10.379(3)
_cell_length_c                   8.5247(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2737.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       700000
_cell_measurement_reflns_used    1535
_cell_measurement_theta_min      5.52
_cell_measurement_theta_max      23.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         700000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            9630
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.537
_diffrn_reflns_theta_max         25.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.386
_diffrn_measured_fraction_theta_full 0.396
_diffrn_reflns_Laue_measured_fraction_max 0.386
_diffrn_reflns_Laue_measured_fraction_full 0.396
_diffrn_reflns_point_group_measured_fraction_max 0.386
_diffrn_reflns_point_group_measured_fraction_full 0.396
_reflns_number_total             984
_reflns_number_gt                515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0912P)²+4.4079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         984
_refine_ls_number_parameters     125
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.1963
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.45743(14) 0.7563(8) -0.0004(6) 0.081(3) Uani 1 1 d D . . . .
C2M C 0.41838(18) 0.6249(9) 0.1839(8) 0.060(2) Uiso 1 1 d D . . . .
H2M H 0.4150 0.6780 0.2782 0.072 Uiso 1 1 calc R U . A 1
C6M C 0.37697(18) 0.6325(11) 0.0958(9) 0.076(3) Uiso 1 1 d . . . . .
H6M1 H 0.3776 0.5703 0.0108 0.091 Uiso 1 1 calc R U . . .
H6M2 H 0.3744 0.7176 0.0497 0.091 Uiso 1 1 calc R U . . .
C7M C 0.33793(15) 0.6069(9) 0.1959(6) 0.074(5) Uani 1 1 d G . . . .
C8M C 0.3181(2) 0.4866(8) 0.1932(7) 0.087(6) Uani 1 1 d G . . . .
H8M H 0.3293 0.4227 0.1253 0.104 Uiso 1 1 d G U . . .
C9M C 0.2830(2) 0.4575(8) 0.2854(9) 0.104(6) Uani 1 1 d G . . . .
H9M H 0.2707 0.3744 0.2819 0.125 Uiso 1 1 d G U . . .
C10M C 0.26586(16) 0.5505(11) 0.3836(7) 0.107(7) Uani 1 1 d G . . . .
H10M H 0.2416 0.5309 0.4469 0.128 Uiso 1 1 d G U . . .
C11M C 0.2843(2) 0.6740(10) 0.3898(7) 0.106(7) Uani 1 1 d G . . . .
H11M H 0.2725 0.7379 0.4560 0.127 Uiso 1 1 d G U . . .
C12M C 0.3206(2) 0.7004(7) 0.2962(8) 0.082(5) Uani 1 1 d G . . . .
H12M H 0.3335 0.7826 0.3008 0.098 Uiso 1 1 d G U . . .
C1M C 0.4579(3) 0.6732(13) 0.0996(13) 0.062(3) Uiso 0.879(7) 1 d D U P B 1
C3M C 0.4343(2) 0.4908(11) 0.2389(12) 0.065(3) Uiso 0.879(7) 1 d D U P B 1
H3M1 H 0.4289 0.4265 0.1587 0.077 Uiso 0.879(7) 1 calc R U P B 1
H3M2 H 0.4195 0.4652 0.3343 0.077 Uiso 0.879(7) 1 calc R U P B 1
C4M C 0.4835(2) 0.5043(12) 0.2688(10) 0.060(3) Uiso 0.879(7) 1 d D U P B 1
H4M1 H 0.4891 0.5249 0.3779 0.071 Uiso 0.879(7) 1 calc R U P B 1
H4M2 H 0.4985 0.4251 0.2424 0.071 Uiso 0.879(7) 1 calc R U P B 1
C5M C 0.4977(2) 0.6117(10) 0.1647(9) 0.053(2) Uiso 0.879(7) 1 d D U P B 1
C13M C 0.53654(18) 0.6620(10) 0.1331(9) 0.058(2) Uiso 0.879(7) 1 d D U P B 1
H13M H 0.5362 0.7291 0.0607 0.069 Uiso 0.879(7) 1 calc R U P B 1
C14M C 0.57893(13) 0.6298(7) 0.1925(7) 0.058(2) Uiso 0.879(7) 1 d DG U P B 1
C15M C 0.58635(15) 0.5365(7) 0.3098(7) 0.063(3) Uiso 0.879(7) 1 d DG U P B 1
H15M H 0.5627 0.4905 0.3519 0.076 Uiso 0.879(7) 1 d G U P B 1
C16M C 0.62854(18) 0.5109(7) 0.3648(8) 0.080(3) Uiso 0.879(7) 1 d G U P B 1
H16M H 0.6332 0.4478 0.4429 0.096 Uiso 0.879(7) 1 d G U P B 1
C17M C 0.66338(13) 0.5789(8) 0.3036(8) 0.082(3) Uiso 0.879(7) 1 d G U P B 1
H17M H 0.6917 0.5632 0.3416 0.098 Uiso 0.879(7) 1 d G U P B 1
C18M C 0.65648(15) 0.6699(7) 0.1866(7) 0.077(3) Uiso 0.879(7) 1 d G U P B 1
H18M H 0.6801 0.7160 0.1450 0.093 Uiso 0.879(7) 1 d G U P B 1
C19M C 0.61482(17) 0.6932(7) 0.1308(7) 0.070(3) Uiso 0.879(7) 1 d DG U P B 1
H19M H 0.6107 0.7535 0.0492 0.084 Uiso 0.879(7) 1 d G U P B 1
C1D C 0.4552(13) 0.662(3) 0.086(6) 0.068(19) Uiso 0.121(7) 1 d D U P B 2
C3D C 0.4251(12) 0.502(4) 0.272(7) 0.058(16) Uiso 0.121(7) 1 d D U P B 2
H3D1 H 0.4108 0.4300 0.2216 0.069 Uiso 0.121(7) 1 calc R U P B 2
H3D2 H 0.4151 0.5089 0.3798 0.069 Uiso 0.121(7) 1 calc R U P B 2
C4D C 0.4744(12) 0.490(5) 0.263(3) 0.056(10) Uiso 0.121(7) 1 d D U P B 2
H4D1 H 0.4838 0.4015 0.2744 0.068 Uiso 0.121(7) 1 calc R U P B 2
H4D2 H 0.4885 0.5428 0.3424 0.068 Uiso 0.121(7) 1 calc R U P B 2
C5D C 0.4826(6) 0.542(2) 0.097(2) 0.050(9) Uiso 0.121(7) 1 d D U P B 2
C13D C 0.5276(6) 0.565(3) 0.029(3) 0.051(9) Uiso 0.121(7) 1 d D U P B 2
H13D H 0.5253 0.6465 -0.0278 0.061 Uiso 0.121(7) 1 calc R U P B 2
C14D C 0.5669(8) 0.579(4) 0.128(4) 0.059(13) Uiso 0.121(7) 1 d DG U P B 2
C15D C 0.5772(11) 0.497(4) 0.255(5) 0.074(15) Uiso 0.121(7) 1 d DG U P B 2
H15D H 0.5571 0.4336 0.2872 0.088 Uiso 0.121(7) 1 d G U P B 2
C16D C 0.6170(12) 0.509(6) 0.334(5) 0.071(15) Uiso 0.121(7) 1 d G U P B 2
H16D H 0.6237 0.4537 0.4186 0.085 Uiso 0.121(7) 1 d G U P B 2
C17D C 0.6465(10) 0.603(6) 0.288(5) 0.095(16) Uiso 0.121(7) 1 d G U P B 2
H17D H 0.6731 0.6128 0.3420 0.114 Uiso 0.121(7) 1 d G U P B 2
C18D C 0.6369(11) 0.683(6) 0.162(5) 0.090(16) Uiso 0.121(7) 1 d G U P B 2
H18D H 0.6569 0.7466 0.1303 0.108 Uiso 0.121(7) 1 d G U P B 2
C19D C 0.5979(10) 0.669(4) 0.082(4) 0.075(15) Uiso 0.121(7) 1 d DG U P B 2
H19D H 0.5921 0.7222 -0.0049 0.090 Uiso 0.121(7) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1M 1.213(10) . ?
O1M C1D 1.225(17) . ?
C2M C1D 1.464(18) . ?
C2M C6M 1.487(8) . ?
C2M C3D 1.50(2) . ?
C2M C1M 1.505(9) . ?
C2M C3M 1.549(11) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.502(8) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.3916 . ?
C7M C12M 1.3999 . ?
C8M C9M 1.3741 . ?
C8M H8M 0.9451 . ?
C9M C10M 1.3838 . ?
C9M H9M 0.9438 . ?
C10M C11M 1.4047 . ?
C10M H10M 0.9465 . ?
C11M C12M 1.4029 . ?
C11M H11M 0.9451 . ?
C12M H12M 0.9434 . ?
C1M C5M 1.494(10) . ?
C3M C4M 1.549(10) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.491(12) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.336(9) . ?
C13M C14M 1.445(7) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.3932 . ?
C14M C15M 1.4118 . ?
C15M C16M 1.4119 . ?
C15M H15M 0.9438 . ?
C16M C17M 1.3901 . ?
C16M H16M 0.9451 . ?
C17M C18M 1.3898 . ?
C17M H17M 0.9488 . ?
C18M C19M 1.3949 . ?
C18M H18M 0.9423 . ?
C19M H19M 0.9448 . ?
C1D C5D 1.516(18) . ?
C3D C4D 1.53(2) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.535(18) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.527(17) . ?
C5D C13D 1.574(14) 5_665 ?
C13D C14D 1.489(16) . ?
C13D C5D 1.574(14) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.3967 . ?
C14D C15D 1.4096 . ?
C15D C16D 1.4103 . ?
C15D H15D 0.9461 . ?
C16D C17D 1.3933 . ?
C16D H16D 0.9437 . ?
C17D C18D 1.3877 . ?
C17D H17D 0.9478 . ?
C18D C19D 1.3931 . ?
C18D H18D 0.9444 . ?
C19D H19D 0.9436 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1D C2M C6M 112(2) . . ?
C1D C2M C3D 113.9(15) . . ?
C6M C2M C3D 115(2) . . ?
C6M C2M C1M 116.2(7) . . ?
C6M C2M C3M 118.3(8) . . ?
C1M C2M C3M 100.7(6) . . ?
C6M C2M H2M 107.0 . . ?
C1M C2M H2M 107.0 . . ?
C3M C2M H2M 107.0 . . ?
C2M C6M C7M 113.3(6) . . ?
C2M C6M H6M1 108.9 . . ?
C7M C6M H6M1 108.9 . . ?
C2M C6M H6M2 108.9 . . ?
C7M C6M H6M2 108.9 . . ?
H6M1 C6M H6M2 107.7 . . ?
C8M C7M C12M 117.6 . . ?
C8M C7M C6M 120.2(7) . . ?
C12M C7M C6M 122.2(7) . . ?
C9M C8M C7M 122.4 . . ?
C9M C8M H8M 119.0 . . ?
C7M C8M H8M 118.6 . . ?
C8M C9M C10M 119.8 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.1 . . ?
C9M C10M C11M 120.2 . . ?
C9M C10M H10M 120.0 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.8 . . ?
C10M C11M H11M 120.3 . . ?
C7M C12M C11M 121.2 . . ?
C7M C12M H12M 119.3 . . ?
C11M C12M H12M 119.4 . . ?
O1M C1M C5M 125.1(7) . . ?
O1M C1M C2M 124.2(8) . . ?
C5M C1M C2M 110.5(7) . . ?
C2M C3M C4M 106.3(8) . . ?
C2M C3M H3M1 110.5 . . ?
C4M C3M H3M1 110.5 . . ?
C2M C3M H3M2 110.5 . . ?
C4M C3M H3M2 110.5 . . ?
H3M1 C3M H3M2 108.7 . . ?
C5M C4M C3M 105.1(7) . . ?
C5M C4M H4M1 110.7 . . ?
C3M C4M H4M1 110.7 . . ?
C5M C4M H4M2 110.7 . . ?
C3M C4M H4M2 110.7 . . ?
H4M1 C4M H4M2 108.8 . . ?
C13M C5M C4M 132.6(7) . . ?
C13M C5M C1M 119.9(8) . . ?
C4M C5M C1M 107.3(6) . . ?
C5M C13M C14M 130.8(8) . . ?
C5M C13M H13M 114.6 . . ?
C14M C13M H13M 114.6 . . ?
C19M C14M C15M 117.5 . . ?
C19M C14M C13M 118.8(5) . . ?
C15M C14M C13M 123.7(5) . . ?
C14M C15M C16M 121.0 . . ?
C14M C15M H15M 119.3 . . ?
C16M C15M H15M 119.7 . . ?
C17M C16M C15M 119.8 . . ?
C17M C16M H16M 119.9 . . ?
C15M C16M H16M 120.3 . . ?
C18M C17M C16M 119.7 . . ?
C18M C17M H17M 120.2 . . ?
C16M C17M H17M 120.1 . . ?
C17M C18M C19M 120.3 . . ?
C17M C18M H18M 119.7 . . ?
C19M C18M H18M 120.0 . . ?
C14M C19M C18M 121.7 . . ?
C14M C19M H19M 118.9 . . ?
C18M C19M H19M 119.4 . . ?
O1M C1D C2M 126.8(18) . . ?
O1M C1D C5D 131.6(19) . . ?
C2M C1D C5D 100.4(11) . . ?
C2M C3D C4D 100.5(19) . . ?
C2M C3D H3D1 111.7 . . ?
C4D C3D H3D1 111.7 . . ?
C2M C3D H3D2 111.7 . . ?
C4D C3D H3D2 111.7 . . ?
H3D1 C3D H3D2 109.4 . . ?
C3D C4D C5D 101(2) . . ?
C3D C4D H4D1 111.7 . . ?
C5D C4D H4D1 111.7 . . ?
C3D C4D H4D2 111.7 . . ?
C5D C4D H4D2 111.7 . . ?
H4D1 C4D H4D2 109.4 . . ?
C1D C5D C13D 111(2) . . ?
C1D C5D C4D 104.6(18) . . ?
C13D C5D C4D 124(2) . . ?
C1D C5D C13D 115(3) . 5_665 ?
C13D C5D C13D 91.8(14) . 5_665 ?
C4D C5D C13D 111(2) . 5_665 ?
C14D C13D C5D 123(2) . . ?
C14D C13D C5D 129(3) . 5_665 ?
C5D C13D C5D 88.2(14) . 5_665 ?
C14D C13D H13D 104.8 . . ?
C5D C13D H13D 104.8 . . ?
C5D C13D H13D 104.8 5_665 . ?
C19D C14D C15D 117.6 . . ?
C19D C14D C13D 117.8(19) . . ?
C15D C14D C13D 124.2(19) . . ?
C14D C15D C16D 120.7 . . ?
C14D C15D H15D 119.4 . . ?
C16D C15D H15D 119.8 . . ?
C17D C16D C15D 119.9 . . ?
C17D C16D H16D 120.0 . . ?
C15D C16D H16D 120.1 . . ?
C18D C17D C16D 119.8 . . ?
C18D C17D H17D 120.0 . . ?
C16D C17D H17D 120.2 . . ?
C17D C18D C19D 120.0 . . ?
C17D C18D H18D 119.9 . . ?
C19D C18D H18D 120.1 . . ?
C18D C19D C14D 121.8 . . ?
C18D C19D H19D 119.2 . . ?
C14D C19D H19D 118.9 . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_49.3%P_0.7GPa
_database_code_depnum_ccdc_archive 'CCDC 1496290'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_49.3%P_0.7GPa       
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.389 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_49.3%P_0.7GPa       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         16 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   30.841(2)
_cell_length_b                   10.374(3)
_cell_length_c                   8.5367(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2731.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       700000
_cell_measurement_reflns_used    1105
_cell_measurement_theta_min      5.51
_cell_measurement_theta_max      19.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.01827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         700000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            8666
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_av_R_equivalents  0.1501
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.534
_diffrn_reflns_theta_max         25.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.376
_diffrn_measured_fraction_theta_full 0.389
_diffrn_reflns_Laue_measured_fraction_max 0.376
_diffrn_reflns_Laue_measured_fraction_full 0.389
_diffrn_reflns_point_group_measured_fraction_max 0.376
_diffrn_reflns_point_group_measured_fraction_full 0.389
_reflns_number_total             964
_reflns_number_gt                451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1348P)²+7.0563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         964
_refine_ls_number_parameters     110
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.2251
_refine_ls_R_factor_gt           0.1224
_refine_ls_wR_factor_ref         0.3602
_refine_ls_wR_factor_gt          0.3010
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1M O 0.4544(2) 0.7500(12) 0.0074(9) 0.091(5) Uani 1 1 d D . . . .
C2M C 0.4161(3) 0.6214(13) 0.1981(12) 0.076(3) Uiso 1 1 d D . . . .
H2M H 0.4142 0.6766 0.2910 0.091 Uiso 1 1 calc R U . A 1
C6M C 0.3727(3) 0.6262(17) 0.1173(13) 0.096(4) Uiso 1 1 d . . . . .
H6M1 H 0.3690 0.7108 0.0710 0.115 Uiso 1 1 calc R U . . .
H6M2 H 0.3725 0.5635 0.0330 0.115 Uiso 1 1 calc R U . . .
C7M C 0.3356(2) 0.5999(13) 0.2228(9) 0.110(5) Uiso 1 1 d G . . . .
C8M C 0.3162(3) 0.4789(12) 0.2224(11) 0.115(5) Uiso 1 1 d G . . . .
H8M H 0.3272 0.4151 0.1539 0.138 Uiso 1 1 d G U . . .
C9M C 0.2819(3) 0.4490(12) 0.3178(13) 0.129(7) Uani 1 1 d G U . . .
H9M H 0.2698 0.3655 0.3157 0.155 Uiso 1 1 d G U . . .
C10M C 0.2650(2) 0.5419(14) 0.4169(11) 0.126(8) Uani 1 1 d G U . . .
H10M H 0.2412 0.5218 0.4823 0.152 Uiso 1 1 d G U . . .
C11M C 0.2830(3) 0.6660(13) 0.4207(10) 0.123(8) Uani 1 1 d G U . . .
H11M H 0.2714 0.7298 0.4877 0.147 Uiso 1 1 d G U . . .
C12M C 0.3186(3) 0.6932(11) 0.3240(11) 0.111(5) Uiso 1 1 d G . . . .
H12M H 0.3312 0.7758 0.3271 0.133 Uiso 1 1 d G U . . .
C1M C 0.4555(6) 0.665(3) 0.104(4) 0.083(11) Uiso 0.507(13) 1 d D U P B 1
C3M C 0.4326(6) 0.488(2) 0.253(4) 0.087(7) Uiso 0.507(13) 1 d D U P B 1
H3M1 H 0.4254 0.4224 0.1759 0.104 Uiso 0.507(13) 1 calc R U P B 1
H3M2 H 0.4195 0.4646 0.3520 0.104 Uiso 0.507(13) 1 calc R U P B 1
C4M C 0.4828(7) 0.500(3) 0.270(3) 0.077(9) Uiso 0.507(13) 1 d D U P B 1
H4M1 H 0.4905 0.5193 0.3778 0.093 Uiso 0.507(13) 1 calc R U P B 1
H4M2 H 0.4970 0.4211 0.2388 0.093 Uiso 0.507(13) 1 calc R U P B 1
C5M C 0.4959(4) 0.608(2) 0.165(2) 0.055(6) Uiso 0.507(13) 1 d D U P B 1
C13M C 0.5354(4) 0.654(2) 0.129(2) 0.071(6) Uiso 0.507(13) 1 d D U P B 1
H13M H 0.5345 0.7160 0.0499 0.085 Uiso 0.507(13) 1 calc R U P B 1
C14M C 0.5788(3) 0.6287(18) 0.183(2) 0.061(6) Uiso 0.507(13) 1 d DG U P B 1
C15M C 0.5874(4) 0.5368(17) 0.301(2) 0.087(7) Uiso 0.507(13) 1 d DG U P B 1
H15M H 0.5642 0.4918 0.3474 0.104 Uiso 0.507(13) 1 d G U P B 1
C16M C 0.6302(5) 0.5112(19) 0.350(2) 0.099(8) Uiso 0.507(13) 1 d G U P B 1
H16M H 0.6356 0.4490 0.4283 0.119 Uiso 0.507(13) 1 d G U P B 1
C17M C 0.6644(3) 0.578(2) 0.282(2) 0.110(8) Uiso 0.507(13) 1 d G U P B 1
H17M H 0.6931 0.5620 0.3158 0.132 Uiso 0.507(13) 1 d G U P B 1
C18M C 0.6562(4) 0.667(2) 0.164(2) 0.083(7) Uiso 0.507(13) 1 d G U P B 1
H18M H 0.6794 0.7123 0.1181 0.100 Uiso 0.507(13) 1 d G U P B 1
C19M C 0.6140(5) 0.6906(19) 0.1145(19) 0.104(8) Uiso 0.507(13) 1 d DG U P B 1
H19M H 0.6090 0.7499 0.0323 0.125 Uiso 0.507(13) 1 d G U P B 1
C1D C 0.4516(7) 0.653(2) 0.090(4) 0.080(10) Uiso 0.493(13) 1 d D U P B 2
C3D C 0.4260(6) 0.498(2) 0.289(3) 0.075(7) Uiso 0.493(13) 1 d D U P B 2
H3D1 H 0.4118 0.4238 0.2424 0.090 Uiso 0.493(13) 1 calc R U P B 2
H3D2 H 0.4178 0.5052 0.3979 0.090 Uiso 0.493(13) 1 calc R U P B 2
C4D C 0.4761(7) 0.492(3) 0.268(3) 0.087(11) Uiso 0.493(13) 1 d D U P B 2
H4D1 H 0.4907 0.5475 0.3425 0.105 Uiso 0.493(13) 1 calc R U P B 2
H4D2 H 0.4868 0.4042 0.2810 0.105 Uiso 0.493(13) 1 calc R U P B 2
C5D C 0.4823(4) 0.5385(16) 0.1017(16) 0.057(6) Uiso 0.493(13) 1 d D U P B 2
C13D C 0.5261(4) 0.5705(17) 0.0239(17) 0.055(6) Uiso 0.493(13) 1 d D U P B 2
H13D H 0.5221 0.6528 -0.0305 0.066 Uiso 0.493(13) 1 calc R U P B 2
C14D C 0.5672(3) 0.5827(17) 0.1149(17) 0.062(6) Uiso 0.493(13) 1 d DG U P B 2
C15D C 0.5802(4) 0.4957(15) 0.2330(19) 0.068(6) Uiso 0.493(13) 1 d DG U P B 2
H15D H 0.5611 0.4295 0.2647 0.082 Uiso 0.493(13) 1 d G U P B 2
C16D C 0.6212(4) 0.5065(19) 0.3038(19) 0.097(8) Uiso 0.493(13) 1 d G U P B 2
H16D H 0.6297 0.4474 0.3822 0.116 Uiso 0.493(13) 1 d G U P B 2
C17D C 0.6493(4) 0.604(2) 0.2577(19) 0.101(8) Uiso 0.493(13) 1 d G U P B 2
H17D H 0.6767 0.6129 0.3063 0.121 Uiso 0.493(13) 1 d G U P B 2
C18D C 0.6371(5) 0.6894(19) 0.140(2) 0.087(7) Uiso 0.493(13) 1 d G U P B 2
H18D H 0.6561 0.7557 0.1088 0.104 Uiso 0.493(13) 1 d G U P B 2
C19D C 0.5968(5) 0.6770(17) 0.0688(17) 0.100(8) Uiso 0.493(13) 1 d DG U P B 2
H19D H 0.5892 0.7339 -0.0131 0.119 Uiso 0.493(13) 1 d G U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1M C1M 1.207(15) . ?
O1M C1D 1.231(15) . ?
C2M C1D 1.468(15) . ?
C2M C6M 1.506(12) . ?
C2M C1M 1.525(15) . ?
C2M C3D 1.525(18) . ?
C2M C3M 1.546(17) . ?
C2M H2M 0.9800 . ?
C6M C7M 1.482(12) . ?
C6M H6M1 0.9700 . ?
C6M H6M2 0.9700 . ?
C7M C8M 1.3903 . ?
C7M C12M 1.3997 . ?
C8M C9M 1.3721 . ?
C8M H8M 0.9450 . ?
C9M C10M 1.3836 . ?
C9M H9M 0.9429 . ?
C10M C11M 1.4035 . ?
C10M H10M 0.9451 . ?
C11M C12M 1.4008 . ?
C11M H11M 0.9449 . ?
C12M H12M 0.9425 . ?
C1M C5M 1.475(16) . ?
C3M C4M 1.561(17) . ?
C3M H3M1 0.9700 . ?
C3M H3M2 0.9700 . ?
C4M C5M 1.488(17) . ?
C4M H4M1 0.9700 . ?
C4M H4M2 0.9700 . ?
C5M C13M 1.344(15) . ?
C13M C14M 1.441(14) . ?
C13M H13M 0.9300 . ?
C14M C19M 1.3907 . ?
C14M C15M 1.4123 . ?
C15M C16M 1.4085 . ?
C15M H15M 0.9422 . ?
C16M C17M 1.3877 . ?
C16M H16M 0.9455 . ?
C17M C18M 1.3904 . ?
C17M H17M 0.9465 . ?
C18M C19M 1.3915 . ?
C18M H18M 0.9406 . ?
C19M H19M 0.9452 . ?
C1D C5D 1.524(16) . ?
C3D C4D 1.556(17) . ?
C3D H3D1 0.9700 . ?
C3D H3D2 0.9700 . ?
C4D C5D 1.515(17) . ?
C4D H4D1 0.9700 . ?
C4D H4D2 0.9700 . ?
C5D C13D 1.543(13) . ?
C5D C13D 1.579(13) 5_665 ?
C13D C14D 1.491(13) . ?
C13D C5D 1.579(13) 5_665 ?
C13D H13D 0.9800 . ?
C14D C19D 1.3946 . ?
C14D C15D 1.4103 . ?
C15D C16D 1.4075 . ?
C15D H15D 0.9448 . ?
C16D C17D 1.3914 . ?
C16D H16D 0.9442 . ?
C17D C18D 1.3885 . ?
C17D H17D 0.9459 . ?
C18D C19D 1.3905 . ?
C18D H18D 0.9430 . ?
C19D H19D 0.9441 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1D C2M C6M 111.6(15) . . ?
C6M C2M C1M 117.1(13) . . ?
C1D C2M C3D 110.9(12) . . ?
C6M C2M C3D 116.0(14) . . ?
C6M C2M C3M 117.3(13) . . ?
C1M C2M C3M 99.4(12) . . ?
C6M C2M H2M 107.4 . . ?
C1M C2M H2M 107.4 . . ?
C3M C2M H2M 107.4 . . ?
C7M C6M C2M 113.7(9) . . ?
C7M C6M H6M1 108.8 . . ?
C2M C6M H6M1 108.8 . . ?
C7M C6M H6M2 108.8 . . ?
C2M C6M H6M2 108.8 . . ?
H6M1 C6M H6M2 107.7 . . ?
C8M C7M C12M 117.7 . . ?
C8M C7M C6M 119.8(10) . . ?
C12M C7M C6M 122.5(10) . . ?
C9M C8M C7M 122.3 . . ?
C9M C8M H8M 119.0 . . ?
C7M C8M H8M 118.7 . . ?
C8M C9M C10M 119.8 . . ?
C8M C9M H9M 120.1 . . ?
C10M C9M H9M 120.2 . . ?
C9M C10M C11M 120.2 . . ?
C9M C10M H10M 120.0 . . ?
C11M C10M H10M 119.8 . . ?
C12M C11M C10M 118.8 . . ?
C12M C11M H11M 120.8 . . ?
C10M C11M H11M 120.4 . . ?
C7M C12M C11M 121.2 . . ?
C7M C12M H12M 119.4 . . ?
C11M C12M H12M 119.4 . . ?
O1M C1M C5M 123.9(15) . . ?
O1M C1M C2M 123.7(14) . . ?
C5M C1M C2M 111.5(12) . . ?
C2M C3M C4M 106.3(15) . . ?
C2M C3M H3M1 110.5 . . ?
C4M C3M H3M1 110.5 . . ?
C2M C3M H3M2 110.5 . . ?
C4M C3M H3M2 110.5 . . ?
H3M1 C3M H3M2 108.7 . . ?
C5M C4M C3M 105.9(13) . . ?
C5M C4M H4M1 110.5 . . ?
C3M C4M H4M1 110.5 . . ?
C5M C4M H4M2 110.5 . . ?
C3M C4M H4M2 110.5 . . ?
H4M1 C4M H4M2 108.7 . . ?
C13M C5M C1M 122.8(15) . . ?
C13M C5M C4M 130.7(15) . . ?
C1M C5M C4M 106.5(12) . . ?
C5M C13M C14M 134.6(17) . . ?
C5M C13M H13M 112.7 . . ?
C14M C13M H13M 112.7 . . ?
C19M C14M C15M 117.6 . . ?
C19M C14M C13M 120.5(12) . . ?
C15M C14M C13M 121.8(12) . . ?
C16M C15M C14M 121.0 . . ?
C16M C15M H15M 119.5 . . ?
C14M C15M H15M 119.4 . . ?
C17M C16M C15M 119.6 . . ?
C17M C16M H16M 120.0 . . ?
C15M C16M H16M 120.3 . . ?
C16M C17M C18M 119.8 . . ?
C16M C17M H17M 119.9 . . ?
C18M C17M H17M 120.3 . . ?
C17M C18M C19M 120.3 . . ?
C17M C18M H18M 119.9 . . ?
C19M C18M H18M 119.8 . . ?
C14M C19M C18M 121.5 . . ?
C14M C19M H19M 119.0 . . ?
C18M C19M H19M 119.5 . . ?
O1M C1D C2M 126.6(14) . . ?
O1M C1D C5D 129.0(15) . . ?
C2M C1D C5D 104.3(11) . . ?
C2M C3D C4D 100.3(14) . . ?
C2M C3D H3D1 111.7 . . ?
C4D C3D H3D1 111.7 . . ?
C2M C3D H3D2 111.7 . . ?
C4D C3D H3D2 111.7 . . ?
H3D1 C3D H3D2 109.5 . . ?
C5D C4D C3D 102.4(14) . . ?
C5D C4D H4D1 111.3 . . ?
C3D C4D H4D1 111.3 . . ?
C5D C4D H4D2 111.3 . . ?
C3D C4D H4D2 111.3 . . ?
H4D1 C4D H4D2 109.2 . . ?
C4D C5D C1D 103.4(15) . . ?
C4D C5D C13D 125.6(14) . . ?
C1D C5D C13D 110.4(14) . . ?
C4D C5D C13D 112.8(18) . 5_665 ?
C1D C5D C13D 114.5(18) . 5_665 ?
C13D C5D C13D 90.3(10) . 5_665 ?
C14D C13D C5D 122.6(12) . . ?
C14D C13D C5D 123.6(13) . 5_665 ?
C5D C13D C5D 89.7(10) . 5_665 ?
C14D C13D H13D 106.3 . . ?
C5D C13D H13D 106.3 . . ?
C5D C13D H13D 106.3 5_665 . ?
C19D C14D C15D 117.7 . . ?
C19D C14D C13D 117.9(11) . . ?
C15D C14D C13D 124.0(11) . . ?
C16D C15D C14D 120.8 . . ?
C16D C15D H15D 119.7 . . ?
C14D C15D H15D 119.6 . . ?
C17D C16D C15D 119.8 . . ?
C17D C16D H16D 120.1 . . ?
C15D C16D H16D 120.1 . . ?
C18D C17D C16D 119.9 . . ?
C18D C17D H17D 120.0 . . ?
C16D C17D H17D 120.1 . . ?
C17D C18D C19D 120.1 . . ?
C17D C18D H18D 120.0 . . ?
C19D C18D H18D 119.9 . . ?
C18D C19D C14D 121.7 . . ?
C18D C19D H19D 119.3 . . ?
C14D C19D H19D 119.0 . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.040

